Formic Acid → 1-methyl-4-(3-formyl-5H-dibenzo[a,d]cycloheptene-5-ylidene)piperidine

HRID 982508Notes

Reaction equation

HRID 982508 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:14]3[CH:15]=[C:16]([C:19]#N)[CH:17]=[CH:18][C:13]=3[CH:12]=[CH:11][C:10]3[CH:21]=[CH:22][CH:23]=[CH:24][C:9]2=3)[CH2:4][CH2:3]1.C(O)=[O:26]>[Ni].[NH4+]>[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:14]3[CH:15]=[C:16]([CH:19]=[O:26])[CH:17]=[CH:18][C:13]=3[CH:12]=[CH:11][C:10]3[CH:21]=[CH:22][CH:23]=[CH:24][C:9]2=3)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 151657121-methyl-4-(3-cyano-5H-dibenzo[a,d]cycloheptene-5-ylidene)piperidine

Product 1

HCID 151657151-methyl-4-(3-formyl-5H-dibenzo[a,d]cycloheptene-5-ylidene)piperidine

Reagents, catalysts & solvents 1

HCID 57466072Raney nickel ammoniumCatalyst

Procedure

A mixture of 1.70 g of 1-methyl-4-(3-cyano-5H-dibenzo[a,d]cycloheptene-5-ylidene)piperidine (prepared as described in U.S. Pat. No. 3,988,342 (1976)), 1.70 g of Raney nickel-ammonium alloy, and 25 ml of 75% aqueous formic acid was stirred under reflux for 1.5 hours. The cooled mixture was filtered and the filtrate was made basic by the additional of solid sodium bicarbonate. Extraction of the neutralized mixture with chloroform and evaporation of the solvent gave 1.30 g of 1-methyl-4-(3-formyl-5H-dibenzo[a,d]cycloheptene-5-ylidene)piperidine.

Workup

  1. customprepared
  2. temperatureunder reflux for 1.5 hours
  3. filtrationThe cooled mixture was filtered
  4. extractionExtraction of the neutralized mixture
  5. customwith chloroform and evaporation of the solvent

Sources & evidence

ORD record
ord-fc767f07b9ed4f7087f988f9b34c0f57
Source dataset
uspto-grants-1991_02
Patent number
US04996321

Reaction notes

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