Propanenitrile, 3-(methylamino)- → 3-[N-(p-chlorocinnamyl)-methylamino]propionitrile

HRID 261203

Reaction equation

HRID 261203 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][CH2:8]Br)=[CH:4][CH:3]=1.[CH3:12][NH:13][CH2:14][CH2:15][C:16]#[N:17]>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.[OH-].[Na+]>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][CH2:8][N:13]([CH3:12])[CH2:14][CH2:15][C:16]#[N:17])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 69656Propanenitrile, 3-(methylamino)-HCID 53877224p-Chlorocinnamyl bromide

Product 1

HCID 543510083-[N-(p-chlorocinnamyl)-methylamino]propionitrile

Reagents, catalysts & solvents 3

HCID 2724282Benzenemethanaminium, N,N,N-tributyl-, bromideCatalystHCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 116 g of p-chlorocinnamyl bromide in 500 ml of methylene chloride is added dropwise with stirring to a mixture of 42 g of 3-methylamino-propionitrile and 8.9 g of benzyl-tri-(n-butyl)ammonium bromide in 1 liter of methylene chloride and 500 ml of 2 N sodium hydroxide solution at room temperature and under a nitrogen atmosphere, and the emulsion stirred for 65 hours at room temperature. The organic phase is separated, washed with water, dried over sodium sulphate and evaporated to yield 3-[N-(p-chlorocinnamyl)-methylamino]-propionitrile. M.P. 143° [hydrogen oxalate form]

Workup

  1. customThe organic phase is separated
  2. washwashed with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-e42bef5d4dd8458b8cd112224d2d9d0c
Source dataset
uspto-grants-1979_08
Patent number
US04164583

Linked notes

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