Methyl Isobutyl Ketone → HCID 19776764, compound

HRID 1612815Notes

Reaction equation

HRID 1612815 reaction equation
C(C(C)=O)C(C)C.[C:8]1([CH:14](Br)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH:22][CH:23]1[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][CH2:31][O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[N+:39]([O-:41])=[O:40])[CH2:25][CH2:24]1>C(N(CC)CC)C>[C:8]1([CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:22][CH:23]2[CH2:24][CH2:25][N:26]([CH2:29][CH2:30][CH2:31][O:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[N+:39]([O-:41])=[O:40])[CH2:27][CH2:28]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7909Methyl Isobutyl KetoneHCID 236603BromodiphenylmethaneHCID 197767934-Hydroxy-1-[3-(2-nitrophenoxy)propyl]piperidine

Product 1

HCID 19776764HCID 19776764, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Into 270 ml of methyl isobutyl ketone were dissolved 32.1 g of diphenylmethyl bromide, 28.0 g of 4-hydroxy-1-[3-(2-nitrophenoxy)propyl]piperidine and 30.4 g of triethylamine. The resultant solution was heated under reflux with stirring for 15 hours. After cooling, the reaction solution was washed with water, and the solvent was removed under reduced pressure. The residue was eluted with methanol-chloroform (1:50) by silica gel column chromatography to give 33.9 g of oily 4-diphenylmethoxy-1-[3-(2-nitrophenoxy)propyl]piperidine.

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. washthe reaction solution was washed with water
  4. customthe solvent was removed under reduced pressure
  5. washThe residue was eluted with methanol-chloroform (1:50) by silica gel column chromatography

Sources & evidence

ORD record
ord-84453cc1751948179f6350e98e55a3a9
Source dataset
uspto-grants-1993_03
Patent number
US05190959

Reaction notes

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