Potassium Iodide → 1-Benzyl-2,6-diethyl-2,3,6-trimethyl-4-benzamidopiperidine

HRID 1701107Notes

Reaction equation

HRID 1701107 reaction equation
[CH2:1]([C:3]1([CH3:22])[CH:8]([CH3:9])[CH:7]([NH:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][C:5]([CH2:20][CH3:21])([CH3:19])[NH:4]1)[CH3:2].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>S1(=O)(=O)CCCC1.C1(C)C=CC=CC=1>[CH2:23]([N:4]1[C:5]([CH2:20][CH3:21])([CH3:19])[CH2:6][CH:7]([NH:10][C:11](=[O:18])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:8]([CH3:9])[C:3]1([CH2:1][CH3:2])[CH3:22])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 22486017N-(2,6-Diethyl-2,3,6-trimethylpiperidin-4-yl)benzamide

Product 1

HCID 203483301-Benzyl-2,6-diethyl-2,3,6-trimethyl-4-benzamidopiperidine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 31347SulfolaneSolvent

Procedure

20 g of 2,6-diethyl-2,3,6-trimethyl-4-benzamidopiperidine (compound no. 9), 12.5 g of benzylbromide, 1 g of potassium iodide and 20 g of potassium carbonate are stirred in 200 ml of tetrahydrothiophene dioxide (sulpholane) at 110° C. for 4 days. Thereafter the reaction mixture is diluted with 200 ml of toluene, cooled to room temperature and purified by filtration. The filtrate is washed four times with about 200 ml of water, the toluene phase is dried over sodium sulfate and evaporated under vacuum. Crystallization of the residue from acetic acid ethyl ester yields 1-benzyl-2,6-diethyl-2,3,6-trimethyl-4-benzamidopiperidine (compound no. 48); m.p. 234°-236° C.

Workup

  1. filtrationpurified by filtration
  2. washThe filtrate is washed four times with about 200 ml of water
  3. dry with materialthe toluene phase is dried over sodium sulfate
  4. customevaporated under vacuum
  5. customCrystallization of the residue from acetic acid ethyl ester

Sources & evidence

ORD record
ord-b3576292e75e412ab03c0bf3c6f01fdc
Source dataset
uspto-grants-1980_03
Patent number
US04191683

Reaction notes

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