Ammonium Chloride → 1-Benzyl-4-(3-phenyl-2-hydroxypropyl)piperidine

HRID 380498Notes

Reaction equation

HRID 380498 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH:15]=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([Mg]Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[NH4+].[Cl-]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH:15]([OH:16])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 100136024-Piperidineacetaldehyde, 1-(phenylmethyl)-HCID 178418336HCID 178418336, compound

Product 1

HCID 183647871-Benzyl-4-(3-phenyl-2-hydroxypropyl)piperidineYield 94.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4 g (18.24 mmol) of 1-Benzyl-4-(2-oxoethyl)piperidine in 40 mL of THF at 0° C. was added 20 mL (36.5 mmol) of benzyl magnesium chloride (2M in THF, Aldrich). THe reaction mixture was warmed to rt and stirred for 30 min. The reaction mixture was poured into 100 mL of sat'd NH4Cl solution and extracted with EtOAc. The combined organic fractions were washed with sat'd Nacl solution, and dried over MgSO4 and filtered. The filtrate was concentrated and purified by chromatography (silica, hexanes:ehtyl acetate, 4:1) to give 5.32 g of the title compound.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic fractions were washed with sat'd Nacl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by chromatography (silica, hexanes:ehtyl acetate, 4:1)

Sources & evidence

ORD record
ord-1fd4a19f1b7d43fa8320dbf928fb6f74
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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