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

HRID 48322ノート

反応式

HRID 48322 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c5827297ba8e4401a66e1b3c9577afa6
出典データセット
uspto-grants-2004_03
特許番号
US06703387B2

反応ノート

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