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

HRID 1638806

反応式

HRID 1638806 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-990e660e52254e7083b413c2a48bc001
出典データセット
uspto-grants-1989_11
特許番号
US04880809

関連ノート

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