Benzylamine → (Benzylamino)acetaldehyde diethyl acetal

HRID 1388512Notes

Reaction equation

HRID 1388512 reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5]Cl)[CH3:2].[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+]>O>[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][NH:17][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 121282-Chloro-1,1-diethoxyethaneHCID 14798Sodium Hydroxide

Product 1

HCID 521961(Benzylamino)acetaldehyde diethyl acetal

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of chloroacetaldehyde diethyl acetal (50 g, 0.328 mol), and benzylamine (150.0 g, 1.4 mol) was heated at 130° for 3 h. The mixture was then left at ambient temperature overnight. Next day, water (150 ml) was added, and the resulting solution was basified with sodium hydroxide solution (25 ml, 10 M). The mixture was then extracted with ether (2×100 ml), and the extracts were combined and dried over magnesium sulphate. Evaporation of the ether under reduced pressure afforded a brown oil which was distilled to afford N-benzylaminoacetaldehyde diethyl acetal, b.p. 148°-150°/20 mmHg.

Workup

  1. temperaturewas heated at 130° for 3 h
  2. extractionThe mixture was then extracted with ether (2×100 ml)
  3. dry with materialdried over magnesium sulphate
  4. customEvaporation of the ether under reduced pressure
  5. customafforded a brown oil which
  6. distillationwas distilled

Sources & evidence

ORD record
ord-c000f023436945e885712a11a3538225
Source dataset
uspto-grants-1984_02
Patent number
US04431815

Reaction notes

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