Water → HCID 54307479, compound

HRID 1419911Notes

Reaction equation

HRID 1419911 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)[Cl:2].[CH2:6]([C:13]1([OH:19])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O>C(OCC)C.C(Cl)Cl>[CH2:6]([C:13]1([OH:19])[CH2:18][CH2:17][N:16]([CH2:4][CH:3]([OH:5])[CH2:1][Cl:2])[CH2:15][CH2:14]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 962WaterHCID 7835EpichlorohydrinHCID 981524-Benzyl-4-piperidinol

Product 1

HCID 54307479HCID 54307479, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

(rac)-Epichlorohydrin (2.5 ml, 31 mmol) dissolved in diethylether (10 ml) was added at room temperature to a suspension of 4-benzyl-4-hydroxy-piperidine (6.0 g, 31 mmol) in diethylether (40 ml) and CH2Cl2 (40 ml). The mixture was stirred overnight at room temperature, water (50 ml) and CH2Cl2 (50 ml) were added and the organic phase was separated. The water phase was extracted with CH2Cl2, the organic phases were pooled, dried with Na2SO4 and the solvents evaporated. The residue was chromatographed over silica gel (ethyl acetate-MeOH, 9:1) to give 4-benzyl-1-(3-chloro-2-hydroxy-propyl)-piperidin-4-ol (1.0 g, 13%) as a colorless solid, m.p. 194°-195° C. and MS: m/e=(M+H+).

Workup

  1. customthe organic phase was separated
  2. extractionThe water phase was extracted with CH2Cl2
  3. dry with materialdried with Na2SO4
  4. customthe solvents evaporated
  5. customThe residue was chromatographed over silica gel (ethyl acetate-MeOH, 9:1)

Sources & evidence

ORD record
ord-8a11d0ada00b40699f50ad8def36ac68
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

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