Phenethylamine → 2-(4-Dimethylamino-4-phenylcyclohexylidene)-N-phenylethylacetamide

HRID 908926ノート

反応式

HRID 908926 の反応式
ON1C2C=CC=CC=2N=N1.[C:11]1([CH2:17][CH2:18][NH2:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CN1CCOCC1.Cl.[CH3:28][N:29]([CH3:46])[C:30]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:35][CH2:34][C:33](=[CH:36][C:37]([OH:39])=O)[CH2:32][CH2:31]1.C1(N=C=NC2CCCCC2)CCCCC1.[OH-].[Na+]>CN(C)C=O.O>[CH3:46][N:29]([CH3:28])[C:30]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:31][CH2:32][C:33](=[CH:36][C:37]([NH:19][CH2:18][CH2:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:39])[CH2:34][CH2:35]1

参加物

9

反応物 6

HCID 1001PhenethylamineHCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 67386703(4-Dimethylamino-4-phenylcyclohexylidene)acetic acid hydrochloride

生成物 1

HCID 116612722-(4-Dimethylamino-4-phenylcyclohexylidene)-N-phenylethylacetamide収率 62%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

1-Hydroxybenzotriazole (273 mg, 2.0 mmol), 2-phenylethylamine (0.125 ml, 1.0 mmol) and N-methylmorpholine (0.222 ml, 2.0 mmol) were added to a solution of (4-dimethylamino-4-phenylcyclohexylidene)acetic acid hydrochloride (296 mg, 1.0 mmol) in dry dimethylformamide (10 ml) under argon. The solution was cooled to 0° C. and dicyclohexylcarbodiimide (417 mg, 2.0 mmol) was added. The reaction mixture was stirred at RT for 10 d. Working up of the mixture was carried out by separating off the urea which had precipitated out and introducing the filtrate into a mixture of saturated NaCl solution (40 ml) and saturated NaHCO3 solution (10 ml). Still further urea thereby precipitated out and was separated off. 5 M sodium hydroxide solution (4 ml, 20 mmol) was added to the aqueous phase and the mixture was diluted with water (300 ml) and stored at 5° C. for 3 d. The product thereby precipitated out as a colourless solid in a yield of 62% (223 mg) and with an m.p. of 153-155° C.

後処理

  1. customby separating off the urea which
  2. customhad precipitated out
  3. additionintroducing the filtrate
  4. additioninto a mixture of saturated NaCl solution (40 ml) and saturated NaHCO3 solution (10 ml)
  5. customStill further urea thereby precipitated out and
  6. customwas separated off
  7. waitstored at 5° C. for 3 d
  8. customThe product thereby precipitated out as a colourless solid in a yield of 62% (223 mg) and with an m.p. of 153-155° C.

出典と根拠

ORDレコード
ord-f9a959495eea4d97b6f1a12a92e01653
出典データセット
uspto-grants-2011_09
特許番号
US08017630B2

反応ノート

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