Diethylamine → N,N-Diethyl-p-vinylphenethylamine

HRID 1106129

Reaction equation

HRID 1106129 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH2:10])=[CH:5][CH:4]=1)=[CH2:2].C1CCCCC1.[CH2:17]([NH:19][CH2:20][CH3:21])[CH3:18]>C([Li])CCC.CO>[CH2:17]([N:19]([CH2:2][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH2:10])=[CH:5][CH:4]=1)[CH2:20][CH3:21])[CH3:18]

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 8078Cyclohexane2×HCID 66041p-Divinylbenzene

Product 1

HCID 3015378N,N-Diethyl-p-vinylphenethylamineYield 71.4%

Reagents, catalysts & solvents 2

HCID 178418339ButyllithiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

In a 200 ml three necked flask were placed 26 g of p-divinylbenzene and 40 ml of cyclohexane, and to the mixture were further added 40 ml of a cyclohexane solution of an amide-amine complex prepared from 14.8 g of diethylamine and 0.512 g of n-butyllithium. The mixture thus obtained was heated at 50° C. for 3 hours with stirring. Then the reaction solution was added with 10 ml of methanol and subjected to distillation to give 29.0 g of p-diethylaminoethylstyrene having a boiling point of about 84° C./1 mmHg.

Workup

  1. customThe mixture thus obtained
  2. distillationsubjected to distillation

Sources & evidence

ORD record
ord-5b6501fb57794448bc5ae1dffa03bbb3
Source dataset
uspto-grants-1982_01
Patent number
US04311799

Linked notes

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