Potassium Hydroxide → 4-(5H-Dibenzo(a,d)cyclohepten-5-ylidene)piperidine

HRID 2371706Notes

Reaction equation

HRID 2371706 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(OCC)=O)[CH2:18][CH2:17]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>C(O)CCC>[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][NH:19][CH2:20][CH2:21]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 14119533HCID 14119533, compound

Product 1

HCID 1597184-(5H-Dibenzo(a,d)cyclohepten-5-ylidene)piperidineYield 102.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 65.6 g of ethyl 4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinecarboxylate, 32.0 g of potassium hydroxide and 250 ml of n-butanol was refluxed for 2 hrs and concentrated. Water was added to the residue and extracted with toluene. The toluene layer was washed with water, dried and concentrated to give 53.2 g of pale yellow solid, which was recrystallized from methanol to give 47.9 g of colorless needles, mp 145°-147° C.

Workup

  1. temperaturewas refluxed for 2 hrs
  2. concentrationconcentrated
  3. additionWater was added to the residue
  4. extractionextracted with toluene
  5. washThe toluene layer was washed with water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cd4d7f82458d4a32b7daf71d414bb0d7
Source dataset
uspto-grants-1992_03
Patent number
US05095022

Reaction notes

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