Hydrochloric Acid → 1-(5,6-dimethoxy-1H-inden-2-ylcarbonyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride

HRID 1638782

반응식

HRID 1638782 반응식
P(C#N)(=O)(OCC)OCC.[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][C:21]=1[O:22][CH3:23])[CH2:18][C:17]([C:24]([OH:26])=O)=[CH:16]2.[ClH:27].Cl.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:41]=[C:42]([O:46][CH3:47])[C:43]=1[O:44][CH3:45])[CH2:34][N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1.Cl>C(O)C.O.CN(C)C=O.C(N(CC)CC)C>[ClH:27].[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][C:21]=1[O:22][CH3:23])[CH2:18][C:17]([C:24]([N:38]1[CH2:37][CH2:36][N:35]([CH2:34][C:33]3[CH:41]=[C:42]([O:46][CH3:47])[C:43]([O:44][CH3:45])=[C:31]([O:30][CH3:29])[CH:32]=3)[CH2:40][CH2:39]1)=[O:26])=[CH:16]2

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 76257Diethyl cyanophosphonateHCID 103761625,6-dimethoxy-1H-indene-2-carboxylic AcidHCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochloride

생성물 1

HCID 198411941-(5,6-dimethoxy-1H-inden-2-ylcarbonyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride수율 79%

시약·촉매·용매 4

HCID 702Ethanol용매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

Diethyl phosphorocyanidate (0.9 g) is added dropwise to an ice-cooling mixture consisting of 5,6-dimethoxy-1H-indene-2-carboxylic acid (0.8 g), 1-(3,4,5-trimethyoxybenzyl)piperazine dihydrochloride (1.3 g), triethylamine (2 ml) and N,N-dimethylformamide (12 ml) with stirring. The whole mixture is stirred at room temperature for two hours and water is added. The mixture is extracted with ethyl acetate. The extract solution is washed with water, dried and then concentrated under reduced pressure. The residue is purified by silica gel column chromatography (ethyl acetate:hexane:acetone=12:8:5) to give an oily product. This product is converted to the hydrochloride in ethanol to afford 1-(5,6-dimethoxy-1H-inden-2-ylcarbonyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride (1.45 g) as colorless scales, m.p. 245°-250° C. (decomp.).

후처리

  1. temperaturecooling mixture
  2. stirringThe whole mixture is stirred at room temperature for two hours
  3. extractionThe mixture is extracted with ethyl acetate
  4. washThe extract solution is washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel column chromatography (ethyl acetate:hexane:acetone=12:8:5)
  8. customto give an oily product

출처 및 근거

ORD 기록
ord-a5a0f17cc8594deda3d7640ee42b160e
출처 데이터셋
uspto-grants-1989_11
특허 번호
US04880809

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