Hexane → HCID 21502279, compound

HRID 1576514Notes

Reaction equation

HRID 1576514 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.[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C([Li])CCC.CCCCCC>>[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:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[C:10]3[CH:20]=[CH:21][CH:22]=[CH:23][C:9]2=3)[CH2:4][CH2:3]1

Participants

5

Reactant 4

HCID 8058HexaneHCID 8082PiperidineHCID 123688821-Methyl-4-(10-bromo-5H-dibenzo[a,d]cyclohepten5-ylidene)-piperidineHCID 178418339Butyllithium

Product 1

HCID 21502279HCID 21502279, compound

Procedure

1-Methyl-4-(10-bromo-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine, 7.32 g. (0.02 mole) is dissolved in 100 ml. of dry piperidine. To this solution is added slowly 25 ml. of a 1.6M solution of butyl lithium in hexane (0.04 mole) under anhydrous conditions and then stirred and refluxed for 8 hours under anhydrous conditions. The reaction is cooled and poured into 500 ml. of benzene and extracted 6 times with 100 ml. of water. The benzene is dried over anhydrous MgSO4, filtered, and the benzene removed on a rotary evaporator leaving 1-methyl-4-(10-(1-piperidyl)-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine as an oil which still has some solvent in it.

Workup

  1. dissolution(0.02 mole) is dissolved in 100 ml
  2. additionTo this solution is added slowly 25 ml
  3. temperaturerefluxed for 8 hours under anhydrous conditions
  4. temperatureThe reaction is cooled
  5. additionpoured into 500 ml
  6. extractionof benzene and extracted 6 times with 100 ml
  7. dry with materialThe benzene is dried over anhydrous MgSO4
  8. filtrationfiltered
  9. customthe benzene removed on a rotary evaporator

Sources & evidence

ORD record
ord-7e5236bc42b543b39129bc600f229d06
Source dataset
uspto-grants-1976_09
Patent number
US03981876

Reaction notes

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