Water → HCID 19004087, compound

HRID 2225370Notes

Reaction equation

HRID 2225370 reaction equation
[N:1]1([C:7]2[C:8]3[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=3[CH2:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH:17]1[C:11]2[CH2:10][C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]=3[C:7]([N:1]3[CH2:2][CH2:3][N:4]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:5][CH2:6]3)=[N:13][C:12]=2[CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 1512464-(11H-Dibenz(b,e)azepin-6-yl)piperazine

Product 1

HCID 19004087HCID 19004087, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2.77 g of 6-(1-piperazinyl)-11H-dibenz[b,e]azepine, 2.00 g of ethyl bromoacetate and 1.38 g of potassium carbonate in 14 ml of N,N-dimethylformamide was stirred at 70° C. for 3 hrs. After cooling, water was added to the reaction mixture and extracted with ether. The etheral layer was washed with water, dried and concentrated. The residue was chromatographed on silica gel using a mixture of n-hexane and ethyl acetate (2:1 and 1:1) as eluents to give 2.91 g of colorless crystals, which were recrystallized from isopropyl ether to give colorless prisms, mp 107°-108° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ether
  3. washThe etheral layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel using
  7. additiona mixture of n-hexane and ethyl acetate (2:1 and 1:1) as eluents

Sources & evidence

ORD record
ord-1a8d8680afc9476a9f54a3f6e587a316
Source dataset
uspto-grants-1994_09
Patent number
US05344828

Reaction notes

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