4-Benzyl-4-piperidinol → HCID 70046349, compound

HRID 1419910Notes

Reaction equation

HRID 1419910 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:19]=[CH:18][C:12]([O:13][CH2:14][C@H:15]3[CH2:17][O:16]3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]([C:27]1([OH:33])[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)C>[CH2:20]([C:27]1([OH:33])[CH2:32][CH2:31][N:30]([CH2:17][C@@H:15]([OH:16])[CH2:14][O:13][C:12]2[CH:18]=[CH:19][C:9]([O:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:10][CH:11]=2)[CH2:29][CH2:28]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 981524-Benzyl-4-piperidinolHCID 12363892HCID 12363892, compound

Product 1

HCID 70046349HCID 70046349, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-{[4-(Phenylmethoxy)phenoxy]methyl}-oxirane (0.55 g, 2.2 mmol) and 4-benzyl-4-hydroxy-piperidine (0.49 g, 2.4 mmol) were dissolved in ethanol (10 ml) and refluxed for 2 h. After evaporation of the solvent, the residue was chromatographed over silica gel (ethyl acetate-MeOH, 9:1) to give (R)-4-benzyl-1-[3-(4-benzyloxy-phenoxy)-2-hydroxy-propyl]-piperidin-4-ol (0.85 g, 88%) as colorless oil. MS: m/e=448.5 (M+H+).

Workup

  1. temperaturerefluxed for 2 h
  2. customAfter evaporation of the solvent
  3. customthe residue was chromatographed over silica gel (ethyl acetate-MeOH, 9:1)

Sources & evidence

ORD record
ord-8527cf358a3740b7a8df9249aa1a4a72
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

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