Water → 4-[4-(Cyclohexyloxy)-1-piperidinyl]benzonitrile

HRID 1816702Notes

Reaction equation

HRID 1816702 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH:10]1([O:16][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH:10]1([O:16][CH:17]2[CH2:18][CH2:19][N:20]([C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=3)[CH2:21][CH2:22]2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 22494678UUKHAODJZMXSOX-UHFFFAOYSA-N

Product 1

HCID 224946954-[4-(Cyclohexyloxy)-1-piperidinyl]benzonitrileYield 53.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-fluorobenzonitrile (1.50 g), 4-(cyclohexyloxy)piperidine (2.40 g) and potassium carbonate (3.3 g) in DMF (30 ml) was stirred at 90-95° C. for 6 hours. The reaction mixture was poured into water (100 ml) and extracted twice with a mixture of ethyl acetate and n-hexane (80 ml:30 ml). The extracts were combined, washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (200 ml) eluting with a mixture of n-hexane and ethyl acetate (6:1 v/v-5:1 v/v). The fractions containing the desired compound were collected and evaporated under reduced pressure to give 4-[4-cyclohexyloxypiperidin-1-yl)benzonitrile (1.90 g).

Workup

  1. extractionextracted twice with a mixture of ethyl acetate and n-hexane (80 ml:30 ml)
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe resulting residue was chromatographed on silica gel (200 ml)
  6. washeluting with a mixture of n-hexane and ethyl acetate (6:1 v/v-5:1 v/v)
  7. additionThe fractions containing the desired compound
  8. customwere collected
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8b0dba4e79d0466e93eac24a01c69953
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

Loading…