Hydrochloric Acid → 1-(3-Butynyl)-4-(4-chlorophenyl)piperidine

HRID 1820009Notes

Reaction equation

HRID 1820009 reaction equation
[CH2:1](O)[CH2:2][C:3]#[CH:4].C(N(CC)CC)C.CS(Cl)(=O)=O.Cl.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].Cl>O1CCCC1.C(#N)C.C(OCC)(=O)C>[CH2:1]([N:29]1[CH2:30][CH2:31][CH:26]([C:23]2[CH:22]=[CH:21][C:20]([Cl:19])=[CH:25][CH:24]=2)[CH2:27][CH2:28]1)[CH2:2][C:3]#[CH:4]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 135663-Butyn-1-OLHCID 31297Methanesulfonyl chlorideHCID 27578434-(4-chlorophenyl)piperidine Hydrochloride

Product 1

HCID 184279681-(3-Butynyl)-4-(4-chlorophenyl)piperidineYield 52.9%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution (50 ml) of 3-butyn-1-ol (700 mg, 10.0 mmol) and triethylamine (2.05 ml, 15 mmol) in tetrahydrofuran was added methanesulfonyl chloride (1.72 g, 15 mmol) at 0° C., and the mixture was stirred at room temperature for 1 hr. Ethyl acetate was added to the reaction mixture, and the mixrture was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. 4-(4-Chlorophenyl)piperidine hydrochloride (2.30 g, 10.0 mmol), potassium carbonate (1.38 g, 10.0 mmol) and acetonitrile (50 ml) were added to the obtained residue, and the mixture was stirred at 60° C. for 16 hrs. 2N Hydrochloric acid was added to the reaction mixture, and the mixture was washed with ethyl acetate. The aqueous layer was basified with 8N aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (1.31 g) as a solid.

Workup

  1. washthe mixrture was washed with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. stirringthe mixture was stirred at 60° C. for 16 hrs
  5. washthe mixture was washed with ethyl acetate
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-93c821f9d74c4993960ddc7c4268a318
Source dataset
uspto-grants-2009_10
Patent number
US07601868B2

Reaction notes

Loading…