Allyl bromide → 2,6-Diethyl-2,3,6-trimethyl-1-(prop-2-en-1-yl)piperidine

HRID 66250Notes

Reaction equation

HRID 66250 reaction equation
[CH2:1]([C:3]1([CH3:13])[CH:8]([CH3:9])[CH2:7][CH2:6][C:5]([CH2:11][CH3:12])([CH3:10])[NH:4]1)[CH3:2].[CH2:14](Br)[CH:15]=[CH2:16].[OH-].[Na+]>C(C1(C)N=C(CCC)CC(CCC)(C)N1)CC>[CH2:16]([N:4]1[C:5]([CH2:11][CH3:12])([CH3:10])[CH2:6][CH2:7][CH:8]([CH3:9])[C:3]1([CH2:1][CH3:2])[CH3:13])[CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 205360782,6-Diethyl-2,3,6-trimethylpiperidine

Product 1

HCID 227545882,6-Diethyl-2,3,6-trimethyl-1-(prop-2-en-1-yl)piperidine

Reagents, catalysts & solvents 1

HCID 227545742,4,6-Tripropyl-2,6-dimethyl-1,2,5,6-tetrahydropyrimidineSolvent

Conditions

Temperature
75 °C

Procedure

36.7 g of 2,6-diethyl-2,3,6-trimethylpiperidine and 30 g of allyl bromide are stirred for 7 days with heating at about 75° C. The reaction mixture is made alkaline by addition of 200 ml of 2 n sodium hydroxide and is extracted with ether. The ethereal solution is dried over K2CO3 and evaporated. The residue is purified by fractional distillation yielding 1-allyl-2,6-diethyl-2,3,6-trimethylpiperidine (Compound No. 4) which distills at 132°-135° C./16 mm Hg.

Workup

  1. extractionis extracted with ether
  2. dry with materialThe ethereal solution is dried over K2CO3
  3. customevaporated
  4. distillationThe residue is purified by fractional distillation

Sources & evidence

ORD record
ord-68ed29c4e365480f93dda058a115384a
Source dataset
uspto-grants-1978_12
Patent number
US04131599

Reaction notes

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