Methyl vinyl ketone → 4-[4-(10,11-Dihydro-5-dibenzo[a,d]-cycloheptenylidene)piperidino]-2-butanone

HRID 616219Notes

Reaction equation

HRID 616219 reaction equation
[CH3:1][C:2]([CH:4]=[CH2:5])=[O:3].[CH:6]1[C:16]2[CH2:15][CH2:14][C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[C:11](=[C:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[C:10]=2[CH:9]=[CH:8][CH:7]=1.C1C2CCC3C=CC=CC=3C(=C3CCN(C)CC3)C=2C=CC=1>C(O)C>[CH:6]1[C:16]2[CH2:15][CH2:14][C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[C:11](=[C:21]3[CH2:22][CH2:23][N:24]([CH2:5][CH2:4][C:2](=[O:3])[CH3:1])[CH2:25][CH2:26]3)[C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6570Methyl vinyl ketoneHCID 1688974-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-methylpiperidineHCID 1201458Desloratadine impurity 24

Product 1

HCID 203715454-[4-(10,11-Dihydro-5-dibenzo[a,d]-cycloheptenylidene)piperidino]-2-butanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.1 g of methylvinylketone are added dropwise at 70° to a solution of 10 g of 4-(10,11-dihydro-5-dibenzo[a,d]cycloheptenylidene)piperidine [M.P. 113°-114°, produced in a manner analogous to that described in Example 4 (a), from 4-(10,11-dihydro-5-dibenzo[a,d]cycloheptenylidene)-1-methylpiperidine] in 100 cc of ethanol, and the mixture is boiled at reflux for 11/2 hours. The reaction mixture is then concentrated by evaporation in a vacuum, the residue is dissolved in acetone, the solution is made acid with hydrogen chloride in ether, is again concentrated by evaporation, and the residue is crystallized first from acetone/ether and then from isopropanol/ether. The hydrochloride of the title compound has an M.P. over 300°.

Workup

  1. customproduced in a manner analogous to
  2. temperatureat reflux for 11/2 hours
  3. concentrationThe reaction mixture is then concentrated by evaporation in a vacuum
  4. dissolutionthe residue is dissolved in acetone
  5. concentrationis again concentrated by evaporation
  6. customthe residue is crystallized first from acetone/ether
  7. customover 300°

Sources & evidence

ORD record
ord-568fc28d2b83448b94f006d634d0637f
Source dataset
uspto-grants-1978_02
Patent number
US04072756

Reaction notes

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