Hydrochloric Acid → 1-Benzyl-4-(2-benzyloxyphenyl)-4-piperidinol

HRID 238273Notes

Reaction equation

HRID 238273 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[Mg]Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl.[OH-].[Na+]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[O:22][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 192201-Benzyl-4-piperidoneHCID 178419625HCID 178419625, compound

Product 1

HCID 118248891-Benzyl-4-(2-benzyloxyphenyl)-4-piperidinolYield 61.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-benzyl-4-piperidone (0.5 g, 2.6 mmol) in THF (10 mL) was cooled to −78° C. and 2-(benzyloxy)phenyl magnesium bromide (3.2 mmol) was added. The mixture was stirred for 0.5 hours then allowed to warm to room temperature. Hydrochloric acid (1 N, 10 mL) was added carefully and the mixture stirred for 0.1 hour before adding a solution of aqueous sodium hydroxide (1 N, 30 mL). The products were extracted into ethyl acetate, dried over magnesium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by flash chromatography on silica eluting with 0-50% ethyl acetate/hexane. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.6 g) as a clear, colourless oil.

Workup

  1. stirringthe mixture stirred for 0.1 hour
  2. extractionThe products were extracted into ethyl acetate
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent removed by evaporation under vacuum
  6. customThe residue was purified by flash chromatography on silica eluting with 0-50% ethyl acetate/hexane
  7. additionThe fractions containing the desired product
  8. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-31c37b59aeb44b2cb67d4ad3f71418fd
Source dataset
uspto-grants-2014_02
Patent number
US08642621B2

Reaction notes

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