Piperidine → 1-[3-(p-Tert.butyl-phenyl)-2-methyl-2-propenyl]-piperidine

HRID 1733266Notes

Reaction equation

HRID 1733266 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[C:12]([CH3:15])[CH2:13]Br)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>CCOCC>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[C:12]([CH3:15])[CH2:13][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 572041753-(p-Tert.butyl-phenyl)-2-methyl-allyl bromide

Product 1

HCID 571057691-[3-(p-Tert.butyl-phenyl)-2-methyl-2-propenyl]-piperidine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

35 g of 3-(p-tert.butyl-phenyl)-2-methyl-allyl bromide in 70 ml of ether are added dropwise to a solution of 24.5 g of piperidine in 100 ml of absolute ether and the mixture is heated at reflux for 16 hours. The piperidine hydrobromide is removed by filtration and rinsed with ether. The ether solution is extracted with 2-N hydrochloric acid and made alkaline with 50% sodium hydroxide. The alkaline-aqueous solution is again extracted with ether, washed with water, dried over sodium sulphate and evaporated. By distillation there is obtained pure 1-[3-(p-tert.butyl-phenyl)-2-methyl-2-propenyl]-piperidine of boiling point 96°-98° C./0.03 Torr.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 16 hours
  3. customThe piperidine hydrobromide is removed by filtration
  4. washrinsed with ether
  5. extractionThe ether solution is extracted with 2-N hydrochloric acid
  6. extractionThe alkaline-aqueous solution is again extracted with ether
  7. washwashed with water
  8. dry with materialdried over sodium sulphate
  9. customevaporated
  10. distillationBy distillation there

Sources & evidence

ORD record
ord-d4413a4440cb404099fed1e0568d214c
Source dataset
uspto-grants-1980_12
Patent number
US04241058

Reaction notes

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