4-Methylmorpholine → 2-(4-dimethylamino-4-phenylcyclohexylidene)-N-[2-(1H-indol-3-yl)-1-methylethyl]acetamide

HRID 908922

반응식

HRID 908922 반응식
ON1C2C=CC=CC=2N=N1.[CH3:11][CH:12]([NH2:23])[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1.CN1CCOCC1.Cl.[CH3:32][N:33]([CH3:50])[C:34]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:39][CH2:38][C:37](=[CH:40][C:41](O)=[O:42])[CH2:36][CH2:35]1.C1(N=C=NC2CCCCC2)CCCCC1.[OH-].[Na+]>CN(C)C=O.O>[CH3:50][N:33]([CH3:32])[C:34]1([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH2:39][CH2:38][C:37](=[CH:40][C:41]([NH:23][CH:12]([CH3:11])[CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)=[O:42])[CH2:36][CH2:35]1

참가 물질

9

반응물 6

HCID 79724-MethylmorpholineHCID 9287(+-)-alpha-MethyltryptamineHCID 10868DicyclohexylcarbodiimideHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 67386703(4-Dimethylamino-4-phenylcyclohexylidene)acetic acid hydrochloride

생성물 1

HCID 115976192-(4-dimethylamino-4-phenylcyclohexylidene)-N-[2-(1H-indol-3-yl)-1-methylethyl]acetamide수율 24%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

1-Hydroxybenzotriazole (456 mg, 3.38 mmol), DL-α-methyltryptamine (0.142 ml, 1.69 mmol) and N-methylmorpholine (0.375 ml, 3.38 mmol) were added to a solution of (4-dimethylamino-4-phenylcyclohexylidene)acetic acid hydrochloride (500 mg, 1.69 mmol) in dry dimethylformamide (10 ml) under argon. The solution was cooled to 0° C. and dicyclohexylcarbodiimide (687 mg, 3.38 mmol) was added. The reaction mixture was stirred at RT for 6 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 (2 ml, 10 mmol) was added to the filtrate and the mixture was diluted with water (200 ml). The product thereby precipitated out as a beige-coloured solid and was to be obtained in a yield of 83% (581 mg). Separation by chromatography on silica gel was carried out with EA/methanol (15:1), (10:1) and (5:1). The less polar diastereoisomer of 2-(4-dimethylamino-4-phenylcyclohexylidene)-N-[2-(1H-indol-3-yl)-1-methylethyl]acetamide were thereby obtained as a colourless solid with an m.p. of 184-187° C. in a yield of 24% (165 mg). It was possible to isolate the more polar diastereoisomer of 2-(4-dimethylamino-4-phenylcyclohexylidene)-N-[2-(1H-indol-3-yl)-1-methylethyl]acetamide as a colourless oil in a yield of 18% (126 mg).—Both amides were diastereoisomerically pure.

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 product thereby precipitated out as a beige-coloured solid
  8. customto be obtained in a yield of 83% (581 mg)
  9. customSeparation by chromatography on silica gel

출처 및 근거

ORD 기록
ord-eb040764bbc34ab6b885d52808d0c2e6
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017630B2

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