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Water → HCID 70047959, compound

HRID 1419908
Notes
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Reaction equation

HRID 1419908 reaction equation
Cl[CH2:2][CH:3]([OH:20])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][CH:7]=1.[CH3:21][C:22]1[CH:35]=[CH:34][C:25]([CH2:26][C:27]2([OH:33])[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].O>CC(=O)CC>[CH2:13]([O:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH:3]([OH:20])[CH2:2][N:30]2[CH2:31][CH2:32][C:27]([CH2:26][C:25]3[CH:24]=[CH:23][C:22]([CH3:21])=[CH:35][CH:34]=3)([OH:33])[CH2:28][CH2:29]2)=[CH:7][CH:8]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 105362424-(4-Methylbenzyl)-piperidin-4-olHCID 133384981-Chloro-3-[4-(phenylmethoxy)phenoxy]-2-propanol

Product 1

HCID 70047959HCID 70047959, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6569
Methyl Ethyl Ketone
Solvent

Procedure

A mixture of (RS)-1-chloro-3-[4-(benzyloxy)phenoxy]-2-propanol (1.0 g, 3.4 mmol), 4-(4-methyl-benzyl)-piperidin-4-ol (0.70 g, 3.4 mmol) and potassium carbonate (0.50 g, 3.6 mmol) in 2-butanone was refluxed for 2 days. It was cooled to room temperature, 50 ml of H2O were added and the organic phase was separated. The water phase was extracted two times with ethyl acetate. The organic phases were then pooled, dried with Na2SO4 and the solvent evaporated. The residue was chromatographed over silica gel (CH2Cl2 --MeOH, 98:2) to give (RS)-1-[3-(4-benzyloxy-phenoxy)-2-hydroxy-propyl]-4-(4-methyl-benzyl)-piperidin-4-ol as a colorless solid (0.75 g, 48%). MS: m/e=462.5 (M+H+)

Workup

  1. temperaturewas refluxed for 2 days
  2. customthe organic phase was separated
  3. extractionThe water phase was extracted two times with ethyl acetate
  4. dry with materialdried with Na2SO4
  5. customthe solvent evaporated
  6. customThe residue was chromatographed over silica gel (CH2Cl2 --MeOH, 98:2)

Sources & evidence

ORD record
ord-6c632db133ab4a2b9abe02815eadb83f
Source dataset
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05889026

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes