Dichloromethane → 1-(3-Cyclohexylpropyl)-4-(p-toluidino)piperidine

HRID 2223878Notes

Reaction equation

HRID 2223878 reaction equation
FC(F)(F)C(O)=O.[C:8]1([CH3:21])[CH:13]=[CH:12][C:11]([NH:14][CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:10][CH:9]=1.Br[CH2:23][CH2:24][CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.C(=O)([O-])[O-].[K+].[K+].ClCCl>CN(C)C=O>[CH:26]1([CH2:25][CH2:24][CH2:23][N:18]2[CH2:19][CH2:20][CH:15]([NH:14][C:11]3[CH:10]=[CH:9][C:8]([CH3:21])=[CH:13][CH:12]=3)[CH2:16][CH2:17]2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 96426(3-Bromopropyl)cyclohexaneHCID 23020925HCID 23020925, compound

Product 1

HCID 230212211-(3-Cyclohexylpropyl)-4-(p-toluidino)piperidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(p-toluidino)piperidine trifluoroacetate (0.7726 g) dissolved in N,N-dimethylformamide (10 mL) were added (3-bromopropyl)cyclohexane (0.57 g) and potassium carbonate (1.02 g). The reaction solution was heated with stirring at 80° C. for 5 hours. Dichloromethane was added to the reaction solution, and the insolubles were filtered off, and then, the solvent was distilled off under reduced pressure. The resulting residue was purified by chromatography [silica gel, dichloromethane-methanol-aqueous ammonia (95:5:0.3)] to give the title compound as a while solid (0.4879 g).

Workup

  1. temperatureThe reaction solution was heated
  2. filtrationthe insolubles were filtered off
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by chromatography [silica gel, dichloromethane-methanol-aqueous ammonia (95:5:0.3)]

Sources & evidence

ORD record
ord-5eb0b05a7fb6446f97e40ce432ca343f
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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