Methanol → HCID 66594897, compound

HRID 1091391Notes

Reaction equation

HRID 1091391 reaction equation
C([N:4]1[CH2:9][CH2:8][CH2:7][C@H:6]([C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=2)[CH2:5]1)(=O)C.O1CCCC1.CO.O.[OH-].[Li+]>O>[Br:16][C:13]1[CH:12]=[CH:11][C:10]([C@H:6]2[CH2:7][CH2:8][CH2:9][NH:4][CH2:5]2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 66594950HCID 66594950, compound

Product 1

HCID 66594897HCID 66594897, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of N-acetyl-(3R)-3-(4-bromophenyl)piperidine (2.88 g, 13.2 mmol) in mixture of tetrahydrofuran (24 ml), methanol (24 ml) and water (12 ml) was added lithium hydroxide monohydrate (3.8 g, 92.4 mmol) and stirred at 95° C. for 2 hours. After filtration, the solvent was removed in vacuo and the residue was partitioned between water and dichloromethane. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give (3R)-3-(4-bromophenyl)piperidine (2.3 g, 87%) as colorless crystals that was used in the next step without further purification.

Workup

  1. filtrationAfter filtration
  2. customthe solvent was removed in vacuo
  3. customthe residue was partitioned between water and dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5ded58f98b0042d597503e1dbbc59dfd
Source dataset
uspto-grants-2012_03
Patent number
US08129377B2

Reaction notes

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