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Volumn , Issue 4, 2007, Pages 652-654

One-pot synthesis of primary tert-alkylamines by the addition of organometallic reagents to nitriles mediated by Ti(Oi-Pr)4

Author keywords

Amines; Nitriles; Nucleophilic addition; Organometallic reagents; Titanium tetraisopropoxide

Indexed keywords

ALIPHATIC AMINE; NITRILE; ORGANOMETALLIC COMPOUND; TERT ALKYLAMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; ENVIRONMENTAL TEMPERATURE; GRIGNARD REACTION; ONE POT SYNTHESIS;

EID: 33947217560 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-967980 Document Type: Article

Times cited : (16)

References (17)

1
- 18844460949
- (a) Ritter, J. J.; Kalish, J. J. Am. Chem. Soc. 1948, 70, 4045.
- (1948) J. Am. Chem. Soc , vol.70 , pp. 4045
- Ritter, J.J.¹ Kalish, J.²

2
- 14544307568
- (b) Ritter, J. J.; Kalish, J. J. Am. Chem. Soc. 1948, 70, 4048.
- (1948) J. Am. Chem. Soc , vol.70 , pp. 4048
- Ritter, J.J.¹ Kalish, J.²

3
- 85083258610
- Koziara, A.; Osowska-Parewicka, K.; Zawadzki, S.; Zwierzak, A. Synthesis 1987, 487.
- (1987) Synthesis , pp. 487
- Koziara, A.¹ Osowska-Parewicka, K.² Zawadzki, S.³ Zwierzak, A.⁴

4
- 0001164135
- Koziara, A.; Zwierzak, A. Tetrahedron Lett. 1987, 28, 6513.
- (1987) Tetrahedron Lett , vol.28 , pp. 6513
- Koziara, A.¹ Zwierzak, A.²

5
- 0011037405
- (a) Davis, F. A.; Mancinelli, P. A. J. Org. Chem. 1977, 42, 398.
- (1977) J. Org. Chem , vol.42 , pp. 398
- Davis, F.A.¹ Mancinelli, P.A.²

6
- 0002073441
- (b) Hirao, A.; Hattori, I.; Yamaguchi, K.; Nakahama, S. Synthesis 1982, 461.
- (1982) Synthesis , pp. 461
- Hirao, A.¹ Hattori, I.² Yamaguchi, K.³ Nakahama, S.⁴

7
- 0002202857
- (a) Chastrette, M.; Axiotis, G. P. Synthesis 1980, 889.
- (1980) Synthesis , pp. 889
- Chastrette, M.¹ Axiotis, G.P.²

8
- 85077993374
- (b) Amouroux, R.; Axiotis, G. P. Synthesis 1981, 270.
- (1981) Synthesis , pp. 270
- Amouroux, R.¹ Axiotis, G.P.²

9
- 0001806205
- (a) Henze, H. R.; Allen, B. B.; Leslie, W. B. J. Am. Chem. Soc. 1943, 65, 87.
- (1943) J. Am. Chem. Soc , vol.65 , pp. 87
- Henze, H.R.¹ Allen, B.B.² Leslie, W.B.³

10
- 0010640666
- (b) Henze, H. R.; Allen, B. B. J. Am. Chem. Soc. 1939, 61, 1790.
- (1939) J. Am. Chem. Soc , vol.61 , pp. 1790
- Henze, H.R.¹ Allen, B.B.²

11
- 0000191820
- Ciganek, E. J. Org. Chem. 1992, 57, 4521.
- (1992) J. Org. Chem , vol.57 , pp. 4521
- Ciganek, E.¹

12
- 33748630852
- Chaplinski, V.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 413;
- (1996) Angew. Chem., Int. Ed. Engl , vol.35 , pp. 413
- Chaplinski, V.¹ de Meijere, A.²

13
- 33947219512
- Angew. Chem. 1996, 108, 491.
- (1996) Chem , vol.108 , pp. 491
- Angew¹

14
- 33947225284
- unpublished results
- Massalov, N. V.; Sokolov, V. V., unpublished results.
- Massalov, N.V.¹ Sokolov, V.V.²

15
- 0037205038
- Bertus, P.; Szymoniak, J. J. Org. Chem. 2002, 67, 3965.
- (2002) J. Org. Chem , vol.67 , pp. 3965
- Bertus, P.¹ Szymoniak, J.²

16
- 33947244033
- General Experimental Procedure for the Synthesis of Primary tert-Alkylamines 8-13: To a solution of the nitrile (10 mmol) in Et2O (30-50 mL) was added the respective Grignard reagent as a 1-3 M Et2O solution (3 equiv, and after stirring for 30 min Ti(Oi-Pr)4 (1 equiv) was added successively at r.t. After the mixture had been heated under reflux for 10 h, a 10% aq solution of NaOH (40 mL) was added. Stirring was continued for 15-30 min. The solution was filtered and the filtrate was extracted with Et2O (3 x 30 mL, The combined Et2O layers were concentrated under reduced pressure and the residue was extracted with dilute aq 5% HCl. The combined aqueous layers were washed with Et2O (2 x 30 mL, made basic by addition of aq 10% NaOH and extracted with Et2O 3 x 30 mL, A few drops of concd HCl were added to the combined Et2O phases and Et2O was evaporated to dr
- 21N·HCl (275.8): C, 74.03; H, 8.04; N, 5.08. Found: C, 74.23; H, 8.14; N, 5.19.

17
- 33947261218
- Experimental Procedure for the Synthesis of 1-(2-Furyl)-1-phenyl- n-butylamine Hydrochloride (17f, To the solution of furan (1.7 g, 25 mmol) in THF (10 mL) was added n-BuLi (2.9 M in hexane, 25 mmol) keeping the temperature below -10°C, and the mixture was stirred at r.t. for 4 h to provide a solution of 2-furyllithium. To a solution of butyronitrile (0.69 g, 10 mmol) in Et2O (30 mL) were added successively at ambient temperature PhMgBr (1.1 M in Et2O, 10 mmol) then, after stirring for 30 min, Ti(Oi-Pr)4 (2.84 g, 10 mmol) and finally the solution of 2-furyllithium. After heating under reflux for 10 h, the reaction mixture was worked up as described in the general procedure above. The product 17f was purified by column chromatography on silica gel (50 g, eluting with CHCl3-MeOH (30:1, 1H NMR (250 MHz, DMSO-d 6, δ, 0.93 t, J, 7.2 Hz, 3 H, 1.15-1.45
- 17NO·HCl (251.8): C, 66.79; H, 7.21; N, 5.56. Found: C, 66.69; H, 7.31; N, 5.26.

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