Aminoacetaldehyde dimethyl acetal → HCID 178495888, compound

HRID 129463Notes

Reaction equation

HRID 129463 reaction equation
[CH2:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH:5]=[CH:4][N:3]=[C:2]1[NH2:12].[CH3:13][O:14][CH:15]([O:18][CH3:19])[CH2:16]N>CO>[CH3:13][O:14][CH:15]([O:18][CH3:19])[CH2:16][NH:12][C:2]1[CH2:1][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 13072414HCID 13072414, compound

Product 1

HCID 178495888HCID 178495888, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3.16 g of 1H-3-benzazepin-2-amine, 4.17 g of 2,2-dimethoxyethanamine and 50 ml of methanol was stirred for 16 hours at reflux temperature. The reaction mixture was evaporated and the residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 95:5). The eluent of the desired fraction was evaporated and the residue was stirred in hexane. The precipitate was filtered off, yielding 4.9 g (100% ) of N-(2,2-dimethoxyethyl)-1H-3-benzazepin-2-amine (interm. 28).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. customthe residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 95:5)
  4. customThe eluent of the desired fraction was evaporated
  5. stirringthe residue was stirred in hexane
  6. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-5566145c4aa04a10b1ff9be91f721c82
Source dataset
uspto-grants-1995_11
Patent number
US05468743

Reaction notes

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