Benzyl Bromide → 1-Benzyl-4-cyano-4-phenylpiperidine

HRID 343717Notes

Reaction equation

HRID 343717 reaction equation
Cl.[C:2]1([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O>[C:2]1([C:8]2([C:14]#[N:15])[CH2:9][CH2:10][N:11]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:13]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 30849734-Phenylpiperidine-4-carbonitrile hydrochloride

Product 1

HCID 1914081-Benzyl-4-cyano-4-phenylpiperidine

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

4-Phenyl-4-cyano-piperidine hydrochloride (10 g, 44.9 mmol), Benzyl bromide (5.4 mL, 45.4 mmol), and potassium carbonate (25.2 g, 182.3 mmol) were combined in THF/water (80 mL/20 mL). After 18 hours the reaction mixture was partitioned between water and dichloromethane. The organic layer was separated and extracted with water, dried over MgSO4, filtered and evaporated in vacuo to give a residue. The residue was recrystallized from hexane to give 4-phenyl -4-cyano-1-benzyl-piperidine as a solid: mp=73°-74° C.

Workup

  1. customAfter 18 hours the reaction mixture was partitioned between water and dichloromethane
  2. customThe organic layer was separated
  3. extractionextracted with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give a residue
  8. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-7196131bc85b48c180eb5cb7a5f2c8d7
Source dataset
uspto-grants-1999_01
Patent number
US05861416

Reaction notes

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