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

HRID 1638807Notes

Reaction equation

HRID 1638807 reaction equation
[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.C(N(CC)CC)C.[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:39]=[C:40]([O:44][CH3:45])[C:41]=1[O:42][CH3:43])[C:36](Cl)=[O:37]>C(Cl)Cl>[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:36](=[O:37])[C:35]4[CH:34]=[C:33]([O:32][CH3:31])[C:41]([O:42][CH3:43])=[C:40]([O:44][CH3:45])[CH:39]=4)[CH2:17][CH2:16]3)=[O:14])=[CH:8][C:7]=2[CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 102452311-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)piperazine

Product 1

HCID 98492201-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)-4-(3,4,5-trimethoxybenzoyl)piperazineYield 67.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)piperazine (1.2 g), triethylamine (0.5 g) and methylene chloride (20 ml) is added dropwise, with stirring under ice-cooling, a solution of 3,4,5-trimethoxybenzoyl chloride (1.0 g) in methylene chloride (25 ml). The reaction mixture is stirred for one hour at room temperature. The reaction mixture is pourd into ice-water (100 ml), and extracted with methylene chloride. The organic layer is washed with water, dried and concentrated under reduced pressure. The concentrate is crystallized from ethyl acetatehexane to give 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)-4-(3,4,5-trimethoxybenzoyl)piperazine (1.3 g), as obtained in Example 62, as colorless prisms, m.p. 164°-165° C.

Workup

  1. additionis added dropwise
  2. temperaturecooling
  3. stirringThe reaction mixture is stirred for one hour at room temperature
  4. extractionextracted with methylene chloride
  5. washThe organic layer is washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe concentrate is crystallized from ethyl acetatehexane

Sources & evidence

ORD record
ord-b66aa2bc1aaa43afab4486b296594c86
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

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