Water → HCID 22492869, compound

HRID 1816696Notes

Reaction equation

HRID 1816696 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH3:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH:18]1[CH2:19][CH2:20][N:21]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH2:22][CH2:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 22492917HCID 22492917, compound

Product 1

HCID 22492869HCID 22492869, compoundYield 31.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-fluorobenzonitrile (0.38 g), 4-(5-methoxypentyloxy)piperidine (0.62 g) and potassium carbonate (0.87 g) in DMF (8 ml) was stirred at 90-95° C. for 6 hours. The reaction mixture was poured into water (50 ml) and extracted twice with a mixture of ethyl acetate and n-hexane (50 ml:20 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 (100 ml) eluting with a mixture of n-hexane and ethyl acetate (5:1 v/v-2:1 v/v). The fractions containing the desired compound were collected and evaporated under reduced pressure to give 4-(5-methoxypentyloxy)-N-(4-cyanophenyl)piperidine (294 mg).

Workup

  1. extractionextracted twice with a mixture of ethyl acetate and n-hexane (50 ml:20 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 (100 ml)
  6. washeluting with a mixture of n-hexane and ethyl acetate (5:1 v/v-2:1 v/v)
  7. additionThe fractions containing the desired compound
  8. customwere collected
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-33128028967449338fb67ae4fb3bee4f
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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