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

HRID 908926

반응식

HRID 908926 반응식
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

참가 물질

9

반응물 6

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

생성물 1

HCID 116612722-(4-Dimethylamino-4-phenylcyclohexylidene)-N-phenylethylacetamide수율 62%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-f9a959495eea4d97b6f1a12a92e01653
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017630B2

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