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

HRID 343498Notes

Reaction equation

HRID 343498 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+]>O1CCCC1.O>[CH2:16]([N:11]1[CH2:10][CH2:9][C:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)([C:14]#[N:15])[CH2:13][CH2:12]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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

Alternately, combine 4-phenyl-4-cyano-piperidine hydrochloric acid salt (10 g, 44.9 mmol), benzyl bromide (5.4 mL, 45.4 mmol), and potassium carbonate (25.2g, 182.3 mmol) in tetrahydrofuran/water (80 mL/20 mL). After 18 hours, partition the reaction mixture between water and dichloromethane. Separate The organic layer and extract with water, dry over MgSO4, filter and evaporate invacuo to give a residue. Recrystallize the residue from hexane to give 1-benzyl-4-phenyl-4-cyanopiperidine as a solid: mp; 73°-74° C.

Workup

  1. custompartition the reaction mixture between water and dichloromethane
  2. customSeparate The organic layer
  3. extractionextract with water
  4. dry with materialdry over MgSO4
  5. filtrationfilter
  6. customevaporate invacuo
  7. customto give a residue
  8. customRecrystallize the residue from hexane

Sources & evidence

ORD record
ord-6af9594e2cda42c1a919923860343293
Source dataset
uspto-grants-1999_01
Patent number
US05861417

Reaction notes

Loading…