Tryptamine → 2-(Dimethylamino-4-phenylcyclohexylidene)-N-[2-(1H-indol-3-yl)ethyl]acetamide

HRID 908919

반응식

HRID 908919 반응식
ON1C2C=CC=CC=2N=N1.[NH2:11][CH2:12][CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1.[CH3:23][N:24]1[CH2:29]CO[CH2:26][CH2:25]1.Cl.CN(C)[C:33]1([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)CC[C:36](=[CH:39][C:40](O)=[O:41])[CH2:35][CH2:34]1.C1(N=C=NC2CCCCC2)CCCCC1.[OH-].[Na+]>CN(C)C=O.O>[CH3:29][N:24]([CH:25]1[CH2:26][CH:33]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH2:34][CH2:35][C:36]1=[CH:39][C:40]([NH:11][CH2:12][CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)=[O:41])[CH3:23]

참가 물질

9

반응물 6

HCID 1150TryptamineHCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 67386703(4-Dimethylamino-4-phenylcyclohexylidene)acetic acid hydrochloride

생성물 1

HCID 673864932-(Dimethylamino-4-phenylcyclohexylidene)-N-[2-(1H-indol-3-yl)ethyl]acetamide수율 31%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

1-Hydroxybenzotriazole (182 mg, 1.35 mmol), tryptamine (108 mg, 0.676 mmol) and N-methylmorpholine (0.148 ml, 1.35 mmol) were added to a solution of (4-dimethylamino-4-phenylcyclohexylidene)acetic acid hydrochloride (200 mg, 0.676 mmol) in dry dimethylformamide (10 ml) under argon. The clear solution was cooled to 0° C. and dicyclohexylcarbodiimide (278 mg, 1.35 mmol) was added. The reaction mixture was stirred at RT for 3 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. The filtrate obtained was extracted with ether. 5 M sodium hydroxide solution (2 ml, 10 mmol) was added to the aqueous phase and the mixture was diluted with water (150 ml). The product thereby precipitated out as a colourless solid in a yield of 31% (84 mg).

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. customThe filtrate obtained
  8. extractionwas extracted with ether
  9. customThe product thereby precipitated out as a colourless solid in a yield of 31% (84 mg)

출처 및 근거

ORD 기록
ord-6e76dea21b6e4d438f67f4cda060ca2c
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017630B2

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