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1-(4-fluoro-3-nitrobenzyl)piperidine synthesis

3synthesis methods
-

Yield:-

Reaction Conditions:

with NaBH(OAc)3;acetic acid in 1,2-dichloro-ethane;

Steps:

29.c Example 29

(c) 1-(4-fluoro-3-nitrobenzyl)-piperidine To a 1 L flask containing 24.0 g 4-fluoro-3-nitrobenzaldehyde (142.0 mmol, 1.0 equiv), 400 mL 1,2-dichloroethane and 30 mL AcOH (426.0 mmol, 3.0 equiv) was carefully added a solution of 16.8 mL piperidine (170.4 mmol, 1.2 equiv) in 100 mL 1,2-dichloroethane via a addition funnel over a period of 1 h at 0° C., and then NaBH(OAc)3 (586.0 mmol, 4.0 equiv). After stirring for 12 h, the reaction was acidified (1 N HCl) and washed (2*hexane). The aqueous layer was then basified (solid NaOH), extracted (2*10% MeOH/CH2Cl2), dried (Na2SO4) and concentrated under reduced pressure to give 19.36 g of the product as a yellow liquid (81.3 mmol).

References:

US2003/144286,2003,A1