Acrylonitrile → HCID 28830263, compound

HRID 900051Notes

Reaction equation

HRID 900051 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][C@H:10]([NH2:13])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14](#[N:17])[CH:15]=[CH2:16]>C(O)C>[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][C@H:10]([NH:13][CH2:16][CH2:15][C:14]#[N:17])[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 7855Acrylonitrile2×HCID 1519353(3S)-(+)-1-Benzyl-3-aminopyrrolidine

Product 1

HCID 28830263HCID 28830263, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (S)-1-(phenylmethyl)-3-pyrrolidinamine, (0.115 mol) and 2-propenenitrile (0.115 mol) in ethanol (250 ml) was stirred and refluxed for 2 hours. 2-Propenenitrile (1 g) was added and the reaction mixture was stirred and refluxed for another 2 hours. The solvent was evaporated, yielding 27.0 g of (S)-3-[[1-(phenyl-methyl)-3-pyrrolidinyl]amino]propanenitrile (interm. 5).

Workup

  1. temperaturerefluxed for 2 hours
  2. stirringthe reaction mixture was stirred
  3. temperaturerefluxed for another 2 hours
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-14be50d74344427fa682452512c39c0c
Source dataset
uspto-grants-2008_04
Patent number
US07358239B2

Reaction notes

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