Ethyl chloroformate → HCID 19004083, compound

HRID 2225368Notes

Reaction equation

HRID 2225368 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.Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24].C(=O)([O-])[O-].[K+].[K+]>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]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:5][CH2:6]3)=[N:13][C:12]=2[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 1512464-(11H-Dibenz(b,e)azepin-6-yl)piperazine

Product 1

HCID 19004083HCID 19004083, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3.33 g of 6-(1-piperazinyl)-11H-dibenz[b,e]azepine, 1.63 g of ethyl chloroformate and 1.66 g of potassium carbonate in 20 ml of N,N-dimethylformamide was stirred at 80° C. for 3 hrs. Ice water was added to the reaction mixture and extracted with ether. The ether layer was washed with water, dried and concentrated. The residue was chromatographed on silica gel using a mixture of n-hexane and ethyl acetate (1:2) as an eluent to give 3.14 g of colorless crystals, which were recrystallized from isopropyl ether to give colorless prisms, mp 137°-138° C.

Workup

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

Sources & evidence

ORD record
ord-20098a61eb9048988a7e584496ae909f
Source dataset
uspto-grants-1994_09
Patent number
US05344828

Reaction notes

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