Water → 1-Diphenylmethylpiperidine-4-carboxamide

HRID 362883Notes

Reaction equation

HRID 362883 reaction equation
Br[CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH:15]1[CH2:23][CH2:22][CH:18]([C:19]([NH2:21])=[O:20])[CH2:17][CH2:16]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[C:3]1([CH:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:15]2[CH2:23][CH2:22][CH:18]([C:19]([NH2:21])=[O:20])[CH2:17][CH2:16]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 37724-PiperidinecarboxamideHCID 11430Potassium CarbonateHCID 236603Bromodiphenylmethane

Product 1

HCID 540281161-Diphenylmethylpiperidine-4-carboxamideYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Step 1): Bromodiphenylmethane (2.5 g, 0.01 mol) in DMF (10 ml) was added dropwise at 0°-5° C. to a mixture of isonipecotamide (1.3 g, 0.01 mol) and K2CO3 (1.4 g) in DMF (25 ml). The reaction mixture was stirred for 2 hours at 0°-5° C., then poured into water. The mixture was extracted with ethylether, then the extract was washed with brine, dried (MgSO4) and evaporated to give 1-diphenylmethylpiperidine-4-carboxamide (66%): mp 150° C.

Workup

  1. extractionThe mixture was extracted with ethylether
  2. washthe extract was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-38d65a5bba834bdfa0a0be281076ef11
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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