Water → HCID 18377282, compound

HRID 2301139Notes

Reaction equation

HRID 2301139 reaction equation
Br[CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6](=[O:13])[CH2:5][CH2:4][CH2:3]1.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([CH:2]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[C:6](=[O:13])[CH2:5][CH2:4][CH2:3]2)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 3278659-Bromo-6,7,8,9-tetrahydrobenzocyclohepten-5-one

Product 1

HCID 18377282HCID 18377282, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9-Bromo-6,7,8,9-tetrahydrobenzocyclohepten-5-one (590 mg, 2.5 mmol), 1-t-butoxycarbonylpiperazine (500 mg, 2.7 mmol) and potassium carbonate (510 mg, 3.7 mmol) were stirred overnight in DMF. The reaction solution was mixed with water, the reaction product was extracted with ethyl acetate, washed with water and saturated brine and dried with anhydrous sodium sulfate, the solvent was removed by evaporation under a reduced pressure, and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 450 mg (1.3 mmol, 53%) of the title compound.

Workup

  1. extractionthe reaction product was extracted with ethyl acetate
  2. washwashed with water and saturated brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. customthe solvent was removed by evaporation under a reduced pressure
  5. customthe thus obtained material was separated
  6. custompurified by a silica gel column chromatography

Sources & evidence

ORD record
ord-1f4f9c2d4f6140c195e8aeab660ac257
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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