3,4,5-Trimethoxybenzoic Acid → 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)-4-(3,4,5-trimethoxybenzoyl)piperazine

HRID 1638806

반응식

HRID 1638806 반응식
[CH3:1][O:2][C:3]1[C:4]([O:22][CH3:23])=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][C:9]([C:13]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[O:14])=[CH:8][C:7]=2[CH:21]=1.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([O:37][CH3:38])[C:34]=1[O:35][CH3:36])[C:29](O)=[O:30].C(N(CC)CC)C.P(C#N)(=O)(OCC)OCC>C(OCC)(=O)C.O.CN(C)C=O>[CH3:1][O:2][C:3]1[C:4]([O:22][CH3:23])=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][C:9]([C:13]([N:15]3[CH2:20][CH2:19][N:18]([C:29](=[O:30])[C:28]4[CH:27]=[C:26]([O:25][CH3:24])[C:34]([O:35][CH3:36])=[C:33]([O:37][CH3:38])[CH:32]=4)[CH2:17][CH2:16]3)=[O:14])=[CH:8][C:7]=2[CH:21]=1

참가 물질

8

반응물 4

HCID 83573,4,5-Trimethoxybenzoic AcidHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 102452311-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)piperazine

생성물 1

HCID 98492201-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)-4-(3,4,5-trimethoxybenzoyl)piperazine수율 85.2%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)piperazine (0.8 g), 3,4,5-trimethoxy benzoic acid (0.55 g), triethylamine (0.4 g) and N,N-dimethylformamide (10 ml) is added dropwise diethyl phosphorocyanidate (0.5 g) with stirring under ice-cooling. The reaction mixture is stirred for one hour at room temperature. To the reaction mixture are added water (60 ml) and ethyl acetate (50 ml), followed by shaking. The organic layer is separated, washed with water, dried and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent, ethyl acetate:hexane:acetone=10:5:8) to afford 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)-4-(3,4,5-trimethoxybenzoyl)piperazine (1.1 g). This product is in agreement with the compound obtained by Example 62 in physico-chemical constants.

후처리

  1. temperaturecooling
  2. stirringThe reaction mixture is stirred for one hour at room temperature
  3. stirringby shaking
  4. customThe organic layer is separated
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography (eluent, ethyl acetate:hexane:acetone=10:5:8)

출처 및 근거

ORD 기록
ord-990e660e52254e7083b413c2a48bc001
출처 데이터셋
uspto-grants-1989_11
특허 번호
US04880809

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