Water → HCID 10084344, compound

HRID 622677Notes

Reaction equation

HRID 622677 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[CH:14](Br)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C=O>[CH:14]([N:4]1[CH2:5][CH2:6][CH2:7][CH:2]([OH:1])[CH2:3]1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 232933-HydroxypiperidineHCID 236603Bromodiphenylmethane

Product 1

HCID 10084344HCID 10084344, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.05 g (0.05 mole) of 3-hydroxypiperidine and 13.82 g (0.1 mole) of potassium carbonate were suspended in 100 ml of dimethylformamide. 12.36 g (0.05 mole) of benzhydryl bromide were then added to the mixture, whilst stirring, and the mixture was stirred for 10 hours at room temperature. At the end of this time, the mixture was poured into 700 ml of water and extracted with ethyl acetate. The extracts were washed with water and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The residue was subjected to silica gel column chromatography, and 10.53 g (yield 78%) of the title compound were obtained as a colorless material from the fractions eluted with a 9:1 by volume mixture of toluene and ethyl acetate.

Workup

  1. stirringthe mixture was stirred for 10 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-30b82b96815b4152bef80d138e67d6e5
Source dataset
uspto-grants-1988_09
Patent number
US04772596

Reaction notes

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