Citric Acid → 4-(5-chloro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide citrate

HRID 2357450노트

반응식

HRID 2357450 반응식
[CH3:1][N:2]([CH3:35])[C:3]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([N:13]2[CH2:18][CH2:17][CH:16]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([Cl:28])[CH:26]=4)[NH:21][CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[CH2:5][CH2:4]1.C(O)C.[C:39]([OH:51])(=[O:50])[CH2:40][C:41]([CH2:46][C:47]([OH:49])=[O:48])([C:43]([OH:45])=[O:44])[OH:42]>C(OCC)C>[C:39]([OH:51])(=[O:50])[CH2:40][C:41]([CH2:46][C:47]([OH:49])=[O:48])([C:43]([OH:45])=[O:44])[OH:42].[CH3:1][N:2]([CH3:35])[C:3]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([N:13]2[CH2:14][CH2:15][CH:16]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([Cl:28])[CH:26]=4)[NH:21][CH:20]=3)[CH2:17][CH2:18]2)=[O:12])[CH2:5][CH2:4]1

참가 물질

5

반응물 3

HCID 311Citric AcidHCID 702EthanolHCID 10327255HCID 10327255, 화합물

생성물 1

HCID 103272544-(5-chloro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide citrate

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

The polar diastereoisomer of 4-(5-chloro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide (267 mg, 0.54 mmole) was dissolved in abs. ethanol (7 ml). Citric acid (105.1 mg, 0.55 mmole) was added in one portion at ca. 35° C. while stirring. After stirring for several hours at RT no precipitate was visible. The reaction mixture was reduced to ca. 1 ml of solution and diethyl ether (25 ml) was added in portions. The precipitate formed was filtered off after 18 hours, washed with Et2O (3×2 ml) and dried in vacuo. The polar citrate of 4-(5-chloro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide (324 mg, m.p. 125°-130° C., 88%, Example 19) was a colourless solid.

후처리

  1. stirringAfter stirring for several hours at RT no precipitate
  2. additionwas added in portions
  3. customThe precipitate formed
  4. filtrationwas filtered off after 18 hours
  5. washwashed with Et2O (3×2 ml)
  6. customdried in vacuo

출처 및 근거

ORD 기록
ord-aac63e54445d440282c3c4ae1d405456
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07759385B2

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