2-Bromoethanol → HCID 13558217, compound

HRID 746245Notes

Reaction equation

HRID 746245 reaction equation
[CH2:1](Br)[CH2:2][OH:3].[C:5]1([CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:5]1([CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:12]2[CH2:13][CH2:14][N:15]([CH2:1][CH2:2][OH:3])[CH2:16][CH2:17]2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 882784-Benzhydrylpiperidine

Product 1

HCID 13558217HCID 13558217, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethylene bromohydrin (0.37 ml) was added dropwise with stirring to a mixture of 4-diphenylmethylpiperidine (1 g), potassium carbonate powder (1.1 g) and N,N-dimethylformamide (10 ml), and the mixture was stirred at room temperature for 4 hours. The precipitate was filtered off and the filtrate was concentrated under reduced pressure, followed by addition of water and extraction with dichloromethane. The dichloromethane layer was washed with water and dried (MgSO4) and the solvent was distilled off. The residue was purified by silica gel chromatography [eluent: CH2Cl2 --MeOH (25:1, v/v)] to give 4-diphenylmethyl-1-piperidineethanol as an oil. Yield 1.08 g (91.9%).

Workup

  1. filtrationThe precipitate was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionfollowed by addition of water and extraction with dichloromethane
  4. washThe dichloromethane layer was washed with water
  5. dry with materialdried (MgSO4)
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by silica gel chromatography [eluent

Sources & evidence

ORD record
ord-4d168656632744f282be490703ed9550
Source dataset
uspto-grants-1986_07
Patent number
US04603135

Reaction notes

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