3-Piperidinone, 1-(phenylmethyl)- → 1-Benzyl-3-(4-methoxyphenyl)piperidin-3-ol

HRID 1507183Notes

Reaction equation

HRID 1507183 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([Mg]Br)=[CH:19][CH:18]=1>C1COCC1.[Cl-].[NH4+]>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:20]2[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=2)([OH:14])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 966503-Piperidinone, 1-(phenylmethyl)-HCID 178491912HCID 178491912, compound

Product 1

HCID 137550691-Benzyl-3-(4-methoxyphenyl)piperidin-3-olYield 39.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 1-benzylpiperidin-3-one (5 g, 26 mmol) in THF (30 mL) was added (4-methoxyphenyl)magnesium bromide (0.5 M in ether) (66 mL, 33 mmol) at rt under a nitrogen atmosphere. The reaction was stirred for 2 h and then diluted with sat. ammonium chloride solution and extracted with ethyl acetate (200 mL). The organic layer was dried over Na2SO4 and evaporated under reduced pressure to give crude 1-benzyl-3-(4-methoxyphenyl)piperidin-3-ol (5.1 g, 10.29 mmol, 38.9% yield) with was used in the next step without further purification. LCMS (Method 107): (ES-API), m/z 298.2 (M+H) RT=1.703 min.

Workup

  1. extractionextracted with ethyl acetate (200 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-98f7e20cdff44c619ef47519226e78ef
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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