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

HRID 1449165Notes

Reaction equation

HRID 1449165 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-e784ed6d5f8240e1b5dbc606f6ac7a99
Source dataset
uspto-grants-1980_02
Patent number
US04189495

Reaction notes

Loading…