1-Bromonaphthalene → 1-Methyl-4-(naphthalen-1-yl)piperidin-4-ol

HRID 478194Notes

Reaction equation

HRID 478194 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[CH3:17][N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C:19]1=O.[Cl-].[NH4+].C1C[O:30]CC1>CCCCCC>[OH:30][C:21]1([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[CH:4][CH:3]=2)[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][CH2:20]1

Participants

7

Reactant 5

HCID 70011-BromonaphthaleneHCID 8028Tetrahydrofuran2×HCID 13603N-Methyl-2-piperidoneHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 180012541-Methyl-4-(naphthalen-1-yl)piperidin-4-olYield 63%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a solution of 1-bromonaphthalene (2.7 g, 13 mmol) in THF (40 mL) was added dropwise a 1.63 M solution of n-butyllithium (7.3 mL, 12 mmol) in hexane at −78° C. over 10 minutes. The reaction mixture was then stirred for 30 minutes and a solution of N-methylpiperidone (1.1 g, 10 mmol) in THF (2 mL) was added dropwise to the reaction mixture. After stirring the reaction mixture for 2 hours, a saturated aqueous ammonium chloride(10 mL) was added to the reaction mixture, and the mixture was extracted with chloroform. After drying over anhydrous sodium sulfate, the chloroform layer was concentrated, and the resulting crude crystals were recrystallized from chloroform/hexane to afford the title compound (1.5 g, yield: 63%) as white crystals.

Workup

  1. stirringAfter stirring the reaction mixture for 2 hours
  2. extractionthe mixture was extracted with chloroform
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. concentrationthe chloroform layer was concentrated
  5. customthe resulting crude crystals were recrystallized from chloroform/hexane

Sources & evidence

ORD record
ord-efcd8faf9eba416ba6cee7505fd7fc6b
Source dataset
uspto-grants-2003_11
Patent number
US06642228B1

Reaction notes

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