3-Piperidinone, 1-(phenylmethyl)- → HCID 19424718, compound

HRID 743721Notes

Reaction equation

HRID 743721 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)=[CH:4][CH:3]=1.C([Li])CCC.[CH2:23]([N:30]1[CH2:35][CH2:34][CH2:33][C:32](=[O:36])[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1>[CH2:23]([N:30]1[CH2:35][CH2:34][CH2:33][C:32]([OH:36])([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:17]=[CH:16][C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH:9]=3)=[CH:4][CH:3]=2)[CH2:31]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 966503-Piperidinone, 1-(phenylmethyl)-HCID 54617522-(4-Bromophenyl)naphthaleneHCID 178418339Butyllithium

Product 1

HCID 19424718HCID 19424718, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

2-(4-Bromophenyl)naphthalene (9.29 g, 32.8 mmol) is placed in a round bottom flask under argon and dissolved in anhydrous THF (150 mL). The solution is cooled to -78° C. in a dry ice/acetone bath with stirring. A solution of n-butyl lithium (2.0M, 18.0 ml) is added dropwise and after fifteen minutes 1-benzyl-3-piperidone (8.14 g, 36.08 mmol) in 20 mL of THF is added dropwise with vigorous stirring. After 30 minutes the solution is allowed to warm to room temperature and quenched with saturated ammonium chloride (10 ml). The mixture is diluted with ethyl acetate (500 ml), washed with water and brine. The organic layer is dried over MgSO4 and concentrated on a rotovap. The crude material is purified by silica gel flash column chromatography using 30% ethyl acetate in hexane as the eluant to yield 6.91 g (48%) of 1-benzyl-3-hydroxy-3(4-naphth-2-yl-phenyl)piperidine as a white solid.

Workup

  1. additionis added dropwise with vigorous stirring
  2. temperatureto warm to room temperature
  3. customquenched with saturated ammonium chloride (10 ml)
  4. additionThe mixture is diluted with ethyl acetate (500 ml)
  5. washwashed with water and brine
  6. dry with materialThe organic layer is dried over MgSO4
  7. concentrationconcentrated on a rotovap
  8. customThe crude material is purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-cf03e585c48d4c0bab3fb2a0cc5354be
Source dataset
uspto-grants-1996_09
Patent number
US05556990

Reaction notes

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