Water → HCID 20395314, compound

HRID 261204Notes

Reaction equation

HRID 261204 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH:6]=[CH:7][CH2:8][N:9]([CH3:14])[CH2:10][CH2:11][C:12]#[N:13])=[CH:4][CH:3]=1.[H-].[Na+].O>CN(C)P(=O)(N(C)C)N(C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:8][N:9]([CH3:14])[CH2:10][CH:11]2[C:12]#[N:13])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 543510083-[N-(p-chlorocinnamyl)-methylamino]propionitrile

Product 1

HCID 20395314HCID 20395314, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent2×

Procedure

252 g of 3-[N-(p-chlorocinnamyl)-methylamino]propionitrile in 1 liter of hexamethylphosphoric acid triamide (HMPT) are added dropwise over a period of 11/4 hours at 0°-5° and in a nitrogen atmosphere to a suspension of 36 g of sodium hydride (80% in mineral oil) in 2 liter of HMPT, and the mixture stirred at room temperature for a period of 16 hours. Water is then added to the mixture with ice cooling, the mixture extracted with ether, the organic phase washed with water, dried over sodium sulphate and evaporated to yield 4-(p-chlorobenzyl)-1-methylpyrrolidin-3-carbonitrile. M.P. 170°-172° [hydrogen oxalate form].

Workup

  1. extractionthe mixture extracted with ether
  2. washthe organic phase washed with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-7267177272584de085e9e59097724b53
Source dataset
uspto-grants-1979_08
Patent number
US04164583

Reaction notes

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