Hydrogen Bromide → HCID 14676177, compound

HRID 1638813Notes

Reaction equation

HRID 1638813 reaction equation
C([O:8][C:9]1[C:10]([O:42]CC2C=CC=CC=2)=[CH:11][C:12]2[CH2:18][CH2:17][CH2:16][C:15]([C:19]([N:21]3[CH2:26][CH2:25][N:24]([C:27](=[O:40])[C:28]4[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=4)[CH2:23][CH2:22]3)=[O:20])=[CH:14][C:13]=2[CH:41]=1)C1C=CC=CC=1.Br.O.C(OCC)(=O)C>C(O)(=O)C>[OH:8][C:9]1[C:10]([OH:42])=[CH:11][C:12]2[CH2:18][CH2:17][CH2:16][C:15]([C:19]([N:21]3[CH2:26][CH2:25][N:24]([C:27](=[O:40])[C:28]4[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=4)[CH2:23][CH2:22]3)=[O:20])=[CH:14][C:13]=2[CH:41]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 8857Ethyl AcetateHCID 14676176HCID 14676176, compound

Product 1

HCID 14676177HCID 14676177, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

In acetic acid (40 ml) is dissolved 1-(2,3-dibenzyloxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)-4-(3,4,5-trimethoxybenzoyl)piperazine (4.0 g). To the solution is added an acetic acid solution of 30% hydrobromic acid (40 ml). The mixture is stirred at room temperature for one hour. To the reaction mixture is added water and ethyl acetate, and the mixture is shaken. The organic layer is washed with water and an aqueous solution of sodium hydrogencarbonate, dried and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent, acetone:ethyl acetate:hexane:methylene chloride=2:1:1:1) to give 1-(2,3-dihydroxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)-4-(3,4,5-trimethoxybenzoyl)piperazine (1.25 g). This product is recrystallized from ethyl acetate to give colorless crystals, m.p. 206°-207° C.

Workup

  1. stirringthe mixture is shaken
  2. washThe organic layer is washed with water
  3. dry with materialan aqueous solution of sodium hydrogencarbonate, dried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel column chromatography (eluent, acetone:ethyl acetate:hexane:methylene chloride=2:1:1:1)

Sources & evidence

ORD record
ord-872a3a199d8a452492b7829322c16007
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

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