Cyproheptadine → HCID 14119533, compound

HRID 2371705Notes

Reaction equation

HRID 2371705 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[C:16]3[CH2:21][CH2:20][N:19](C)[CH2:18][CH2:17]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:23](Cl)(=[O:27])[O:24][CH2:25][CH3:26]>C1(C)C=CC=CC=1>[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[C:16]3[CH2:17][CH2:18][N:19]([C:23]([O:24][CH2:25][CH3:26])=[O:27])[CH2:20][CH2:21]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 2913CyproheptadineHCID 10928Ethyl chloroformate

Product 1

HCID 14119533HCID 14119533, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 33.0 g of 4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-methylpiperidine, 74.9 g of ethyl chlorocarbonate and 170 ml of toluene was refluxed for 3.5 hrs. After cooling, the reaction mixture was washed with hydrochloric acid and water, and then dried and concentrated. The residue was solidified by treatment with n-hexane to give 37.4 g of pale yellow crystals, which were recrystallized from ethanol to give slightly yellow needles, mp 123°-124° C.

Workup

  1. temperaturewas refluxed for 3.5 hrs
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with hydrochloric acid and water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d01da9a8e6f2437aa05f1a407db169ca
Source dataset
uspto-grants-1992_03
Patent number
US05095022

Reaction notes

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