Cyproheptadine → 4-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-methylpiperidine

HRID 2294063Notes

Reaction equation

HRID 2294063 reaction equation
[CH3:1][N:2]1[CH2:22][CH2:21][C:5](=[C:6]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH:14]=[CH:13][C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]2=3)[CH2:4][CH2:3]1.[H][H]>C(O)(=O)C.C(O)C.[Pt]=O>[CH:11]1[C:12]2[CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:6](=[C:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:22][CH2:21]3)[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 2

HCID 2913CyproheptadineHCID 178418361HCID 178418361, compound

Product 1

HCID 1688974-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-methylpiperidineYield 94.2%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

Dissolved cyproheptadine (22.2 g, 0.077 mol) in 150 mL of glacial acetic acid and 20 mL of ethanol. Added platinum oxide catalyst (1.0 g), and hydrogenated on Paar shaker at 57 psi of hydrogen pressure for 5 hours. Filtered, and evaporated filtrate to give a solid. Recrystallized crude product from ether-pet ether to give 21.0 g (94% yield) of 4-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-methylpiperidine as a white solid.

Workup

  1. filtrationFiltered
  2. customevaporated filtrate
  3. customto give a solid
  4. customRecrystallized crude product from ether-pet ether

Sources & evidence

ORD record
ord-1fe20fe936ba4d1da56ddeb14dd314bc
Source dataset
uspto-grants-1997_11
Patent number
US05688805

Reaction notes

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