Acetic Acid → HCID 14676180, compound

HRID 1638817Notes

Reaction equation

HRID 1638817 reaction equation
C([O:8][C:9]1[C:41]([O:42][CH3:43])=[CH:40][C:12]2[CH:13]=[C:14]([C:18]([N:20]3[CH2:25][CH2:24][N:23]([C:26](=[O:39])[C:27]4[CH:32]=[C:31]([O:33][CH3:34])[C:30]([O:35][CH3:36])=[C:29]([O:37][CH3:38])[CH:28]=4)[CH2:22][CH2:21]3)=[O:19])[CH2:15][CH2:16][CH2:17][C:11]=2[CH:10]=1)C1C=CC=CC=1.C(O)(=O)C.Br>CCOCC>[OH:8][C:9]1[C:41]([O:42][CH3:43])=[CH:40][C:12]2[CH:13]=[C:14]([C:18]([N:20]3[CH2:21][CH2:22][N:23]([C:26](=[O:39])[C:27]4[CH:32]=[C:31]([O:33][CH3:34])[C:30]([O:35][CH3:36])=[C:29]([O:37][CH3:38])[CH:28]=4)[CH2:24][CH2:25]3)=[O:19])[CH2:15][CH2:16][CH2:17][C:11]=2[CH:10]=1

Participants

5

Reactant 3

HCID 176Acetic Acid2×HCID 260Hydrogen BromideHCID 14676181HCID 14676181, compound

Product 1

HCID 14676180HCID 14676180, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1-(3-benzyloxy-2-methoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)-4-(3,4,5-trimethoxybenzoyl)piperazine (1.7 g), a 30% acetic acid solution of hydrobromic acid (6 ml) and acetic acid (12 ml) is stirred at room temperature for 40 minutes. To the reaction mixture is added ether (100 ml), and the resulting precipitates are collected by filtration. To the precipitates are added ethyl acetate and water. The mixture is shaken, then the organic layer is separated. The organic layer is washed with an aqueous solution of sodium hydrogencarbonate, and water, and dried, followed by distilling off the solvent under reduced pressure. The residue is purified by silica gel column chromatography (eluent, hexane:ethyl acetate:acetone:methylene chloride=1:1:1:1) to give 1-(3-hydroxy-2-methoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)-4-(3,4,5-trimethoxybenzoyl)piperazine (1.2 g). Recrystallization of this product from ethyl acetate affords colorless crystals, m.p. 198°-199° C.

Workup

  1. customthe resulting precipitates
  2. filtrationare collected by filtration
  3. additionTo the precipitates are added ethyl acetate and water
  4. customthe organic layer is separated
  5. washThe organic layer is washed with an aqueous solution of sodium hydrogencarbonate, and water
  6. customdried
  7. distillationby distilling off the solvent under reduced pressure
  8. customThe residue is purified by silica gel column chromatography (eluent, hexane:ethyl acetate:acetone:methylene chloride=1:1:1:1)

Sources & evidence

ORD record
ord-cbe8be8cf5484d518957ed9ad21f6c50
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

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