Mianserin → HCID 19261489, compound

HRID 2225372Notes

Reaction equation

HRID 2225372 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].C[N:8]1[CH2:26][CH2:25][N:11]2[C:12]3[CH:24]=[CH:23][CH:22]=[CH:21][C:13]=3[CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[CH:10]2[CH2:9]1.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[CH2:9]1[CH:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][C:13]3[CH:21]=[CH:22][CH:23]=[CH:24][C:12]=3[N:11]2[CH2:25][CH2:26][N:8]1[C:2]([O:4][CH2:5][CH3:6])=[O:3]

Participants

5

Reactant 3

HCID 4184MianserinHCID 10928Ethyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 19261489HCID 19261489, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Ethyl chloroformate (19.53 g) was added dropwisely to a solution of 9.52 g of 1,2,3,4,10,14b-hexahydro-2-methyldibenzo[c,f]pyrazino[1,2-a]azepine in 48 ml of benzene at refluxed temperature and the mixture was refluxed for 5 hrs. Ice water was added to the reaction mixture and made alkaline with sodium bicarbonate. The mixture was extracted with benzene and the benzene layer was washed with water, dried and concentrated. The residue was chromatographed on silica gel using a mixture of n-hexane and ethyl acetate as an eluent (1:2) to give 8.70 g of pale yellow crystals, which were recrystallized from a mixture of isopropyl ether and n-pentane to give pale yellow prisms, mp 108.5°-109.5° C.

Workup

  1. temperatureat refluxed temperature
  2. temperaturethe mixture was refluxed for 5 hrs
  3. extractionThe mixture was extracted with benzene
  4. washthe benzene layer was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel using
  8. additiona mixture of n-hexane and ethyl acetate as an eluent (1:2)

Sources & evidence

ORD record
ord-4400666a1002444ea2bfe96edc378366
Source dataset
uspto-grants-1994_09
Patent number
US05344828

Reaction notes

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