1-p-Fluorobenzyl-2-nitromethylene-pyrrolidine → 2-Aminomethyl-1-p-fluorobenzyl-pyrrolidine

HRID 236865

Reaction equation

HRID 236865 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][CH2:9][C:8]2=[CH:12][N+:13]([O-])=O)=[CH:4][CH:3]=1>CO.[Ni]>[NH2:13][CH2:12][CH:8]1[CH2:9][CH2:10][CH2:11][N:7]1[CH2:6][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 540091111-p-Fluorobenzyl-2-nitromethylene-pyrrolidine

Product 1

HCID 147090372-Aminomethyl-1-p-fluorobenzyl-pyrrolidineYield 72.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 27 g (0.114 mol) of 1-p-fluorobenzyl-2-nitromethylene-pyrrolidine in 600 ml of methanol is hydrogenated at ambient temperature and atmospheric pressure in the presence of Raney nickel. When the theoretical amount of hydrogen has been absorbed, which requires about one hour, the catalyst is filtered off and the methanol is evaporated from the filtrate. The product which remains is distilled under reduced pressure. 17.2 g (yield: 72%) of 2-aminomethyl-1-p-fluorobenzyl-pyrrolidine are collected as a colourless liquid distilling at 80°-82° under a pressure of 0.01 mm of mercury; this product is used, without further purification, in the next stage of the synthesis.

Workup

  1. customis hydrogenated at ambient temperature
  2. customWhen the theoretical amount of hydrogen has been absorbed
  3. filtrationthe catalyst is filtered off
  4. customthe methanol is evaporated from the filtrate
  5. distillationThe product which remains is distilled under reduced pressure

Sources & evidence

ORD record
ord-5940074a5b9d43528d376418f1a63612
Source dataset
uspto-grants-1979_06
Patent number
US04158060

Linked notes

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