1-Diphenylmethylpiperidine-4-carboxamide → 4-Cyano-1-diphenylmethylpiperidine

HRID 362908Notes

Reaction equation

HRID 362908 reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=O)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O=P(Cl)(Cl)Cl>[C:14]([CH:11]1[CH2:12][CH2:13][N:8]([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][CH2:10]1)#[N:16]

Participants

3

Reactant 1

HCID 540281161-Diphenylmethylpiperidine-4-carboxamide

Product 1

HCID 541733574-Cyano-1-diphenylmethylpiperidine

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

Step 1): A solution of 1-diphenylmethylpiperidine-4-carboxamide (14.79 g, 50 mmol) in POCl3 (300 ml) was refluxed for 3.5 hours. The reaction mixture was concentrated under vacuum. The residue was dissolved into the mixture of sat. NaHCO3 aq. solution and AcOEt. After separation, the aqueous layer was extracted with AcOEt. The combined organic layer was washed with H2O and brine, dried over MgSO4 and then concentrated. The residue was recrystallized from iso-PrOH to give 4-cyano-1-diphenylmethylpiperidine, 12.36 g (89%): mp 219°-230° C.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutionThe residue was dissolved into the mixture of sat. NaHCO3 aq. solution and AcOEt
  3. customAfter separation
  4. extractionthe aqueous layer was extracted with AcOEt
  5. washThe combined organic layer was washed with H2O and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was recrystallized from iso-PrOH

Sources & evidence

ORD record
ord-babb21840340455f9e594b6fad504f7c
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

Loading…