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

HRID 1638808Notes

Reaction equation

HRID 1638808 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:45][CH3:46])[C:41]=1[O:42][CH2:43][CH3:44])[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][CH2:43][CH3:44])=[C:40]([O:45][CH3:46])[CH:39]=4)[CH2:17][CH2:16]3)=[O:14])=[CH:8][C:7]=2[CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 102452311-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)piperazineHCID 19841201HCID 19841201, compound

Product 1

HCID 146761891-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)-4-(3,5-dimethoxy-4-ethoxy-benzoyl)piperazineYield 45.2%

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 3,5-dimethoxy-4-ethoxybenzoyl chloride (1.0 g) in methylene chloride (20 ml). The reaction mixture is then stirred for one hour at room temperature, and then poured into ice-water, followed by extraction with methylene chloride. The organic layer is washed with water, dried and concentrated under reduced pressure. The concentrate is purified by silica gel column chromatography (hexane:ethyl acetate:acetone=1:2:1) to afford 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)-4-(3,5-dimethoxy-4-ethoxy-benzoyl)piperazine (0.9 g). This product is recrystallized from ethyl acetatehexane to give colorless needles, m.p. 171°-172° C.

Workup

  1. additionis added dropwise
  2. temperaturecooling
  3. stirringThe reaction mixture is then stirred for one hour at room temperature
  4. extractionfollowed by extraction with methylene chloride
  5. washThe organic layer is washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe concentrate is purified by silica gel column chromatography (hexane:ethyl acetate:acetone=1:2:1)

Sources & evidence

ORD record
ord-f91722bf7f664dc9bec61ba05095a82d
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

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