Piperidine → HCID 21502279, compound

HRID 917842Notes

Reaction equation

HRID 917842 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH:12]=[C:11](Br)[C:10]3[CH:20]=[CH:21][CH:22]=[CH:23][C:9]2=3)[CH2:4][CH2:3]1.CC(C)([O-])C.[K+].[NH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>C(O)(C)(C)C>[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH:12]=[C:11]([N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[C:10]3[CH:20]=[CH:21][CH:22]=[CH:23][C:9]2=3)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 123688821-Methyl-4-(10-bromo-5H-dibenzo[a,d]cyclohepten5-ylidene)-piperidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 21502279HCID 21502279, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

1-Methyl-4-(10-bromo-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine, 2.87 g. (0.0079 mole), 50 ml. of a 0.4M solution of potassium t-butoxide in t-butanol, and 20 ml. of dry piperidine is stirred and refluxed under anhydrous conditions for 6 hours. The reaction mixture is cooled and partitioned between 350 ml. of benzene and 50 ml. of water. The benzene layer is then extracted 5 more times with 50 ml. each of water. The benzene layer is then dried over anhydrous MgSO4, filtered, and the benzene evaporated. This gives a single spot on t.l.c. and is used directly in the next step.

Workup

  1. temperaturerefluxed under anhydrous conditions for 6 hours
  2. temperatureThe reaction mixture is cooled
  3. custompartitioned between 350 ml
  4. extractionThe benzene layer is then extracted 5 more times with 50 ml
  5. dry with materialThe benzene layer is then dried over anhydrous MgSO4
  6. filtrationfiltered
  7. customthe benzene evaporated
  8. customThis gives a single spot on t.l.c

Sources & evidence

ORD record
ord-729121134d51424a903f66ff69707406
Source dataset
uspto-grants-1976_07
Patent number
US03968115

Reaction notes

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