3,5-Dimethylpiperidine → HCID 57263213, compound

HRID 1395207Notes

Reaction equation

HRID 1395207 reaction equation
[C:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:17])=[C:13]([CH3:16])[CH2:14]Br)=[CH:8][CH:7]=1)([CH2:4][CH3:5])([CH3:3])[CH3:2].[CH3:18][CH:19]1[CH2:24][CH:23]([CH3:25])[CH2:22][NH:21][CH2:20]1>CCOCC>[C:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:17])=[C:13]([CH3:16])[CH2:14][N:21]2[CH2:22][CH:23]([CH3:25])[CH2:24][CH:19]([CH3:18])[CH2:20]2)=[CH:8][CH:7]=1)([CH2:4][CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 1182593,5-DimethylpiperidineHCID 57148770HCID 57148770, compound

Product 1

HCID 57263213HCID 57263213, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

62 G. of 3-(p-tert.-amyl-phenyl)-2,3-dimethyl-allyl bromide in 150 ml. of ether are added dropwise to a solution of 45.2 g. of 3,5-dimethylpiperidine in 200 ml. of absolute ether and the mixture is heated at reflux for 16 hours. The 3,5-dimethylpiperidine hydrobromide is removed by filtration and back-washed 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 sulfate and evaporated. By distillation, there is obtained pure 1-[3-(p-tert.-amylphenyl)-2,3-dimethyl-2-propenyl]-3,5-dimethylpiperidine having a boiling point of 155° C./0.04 Torr.

Workup

  1. temperatureat reflux for 16 hours
  2. customThe 3,5-dimethylpiperidine hydrobromide is removed by filtration
  3. washback-washed with ether
  4. extractionThe ether solution is extracted with 2 N hydrochloric acid
  5. extractionThe alkaline-aqueous solution is again extracted with ether
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. distillationBy distillation

Sources & evidence

ORD record
ord-75d8975e17d446a991804938251707f8
Source dataset
uspto-grants-1980_05
Patent number
US04202894

Reaction notes

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