Water → HCID 22499375, compound

HRID 1989861Notes

Reaction equation

HRID 1989861 reaction equation
Cl.[C:2]1([CH:8]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:9]#[N:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([N:14]2[CH2:15][CH2:16][CH:11]([CH:8]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:9]#[N:10])[CH2:12][CH2:13]2)=[CH:19][CH:20]=1)([O-:26])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 222528504-Piperidineacetonitrile, α-phenyl-, hydrochloride (1:1)

Product 1

HCID 22499375HCID 22499375, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of α-phenyl-4-piperidineacetonitrile monohydrochloride (0.05 mol), 1-fluoro-4-nitrobenzene (0.06 mol) and K2CO3 (0.15 mol) in DMF (200 ml) was stirred at 50° C. for 4 hours, cooled, poured out into water and extracted with DCM. The organic layer was separated, washed with water, dried, filtered and the solvent was evaporated. The residue was crystallized from DIPE. The precipitate was filtered off and dried, yielding 10.7 g of (±)-1-(4-nitrophenyl)-α-phenyl-4-piperidineacetonitrile (intermediate 15, mp. 118° C.).

Workup

  1. temperaturecooled
  2. extractionextracted with DCM
  3. customThe organic layer was separated
  4. washwashed with water
  5. customdried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was crystallized from DIPE
  9. filtrationThe precipitate was filtered off
  10. customdried

Sources & evidence

ORD record
ord-98bae33066d14d878cd9174e12bf4191
Source dataset
uspto-grants-2010_01
Patent number
US07642378B2

Reaction notes

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