Ethylmorpholine → N-methoxy-N-methyl-2-phenethylbenzamide

HRID 48322Notes

Reaction equation

HRID 48322 reaction equation
[CH2:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11](O)=[O:12])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N1CCOCC1)C.Cl.[CH3:50][NH:51][O:52][CH3:53]>ClCCl>[CH3:53][O:52][N:51]([CH3:50])[C:11](=[O:12])[C:10]1[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=1[CH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 78603o-Phenethylbenzoic acidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 22742379N-methoxy-N-methyl-2-phenethylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3 g (13.2 mmol) of 2-phenethylbenzoic acid, 3.8 g (19.8 mmol) of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride, 2.7 g (20.0 mmol) of 1-hydroxybenzotriazole hydrate, 3 ml (23 mmol) of N-ethylmorpholine and 1.94 g (19.9 mmol) of N,O-dimethylhydroxylamine hydrochloride was stirred in 50 ml of dichloromethane at room temperature for 2 hours. The solution was diluted with dichloromethane and washed sequentially with saturated aqueous citric acid solution and saturated aqueous sodium bicarbonate solution, dried over magnesium sulphate, filtered and evaporated to afford N-methoxy-N-methyl-2-phenethylbenzamide as a colorless oil. To a solution of 1 g (3.7 mmol) of this oil in 10 ml tetrahydrofuran at 0° C. was added 2.2 ml of a 1M solution of lithium aluminium hydride in tetrahydrofuran. The solution was stirred at 0° C. for 25 minutes and saturated aqueous potassium hydrogensulphate and ether were then added and the mixture stirred at room temperature for 30 minutes. The layers were separated and the organic layer washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulphate, filtered and evaporated to afford 2-phenethyl-benzaldehyde as a colorless oil which was used directly without further purification.

Workup

  1. washwashed sequentially with saturated aqueous citric acid solution and saturated aqueous sodium bicarbonate solution
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-c5827297ba8e4401a66e1b3c9577afa6
Source dataset
uspto-grants-2004_03
Patent number
US06703387B2

Reaction notes

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