Hydrochloric Acid → 4-(2,3-Dichlorophenyl)-1-propylpiperidin-4-OL

HRID 2105935Notes

Reaction equation

HRID 2105935 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1([OH:15])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+].I[CH2:23][CH2:24][CH3:25].Cl>C(#N)C>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1([OH:15])[CH2:14][CH2:13][N:12]([CH2:23][CH2:24][CH3:25])[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 627881684-(2,3-Dichlorophenyl)piperidin-4-ol

Product 1

HCID 115801144-(2,3-Dichlorophenyl)-1-propylpiperidin-4-OL

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation according to Example 2: 4-(2,3-dichlorophenyl)piperidin-4-ol (0.43 g, 1.75 mmol), acetonitrile (20 ml), potassium carbonate (0.59 g, 4.3 mmol), iodopropane (0.15 ml, 1.9 mmol). Yield: 0.29 g, 57%. The amine was converted to the hydrochloric acid salt and recrystallized from ethanol/diethyl ether: M.p. 181-183° C. MS m/z (relative intensity, 70 eV) 289 (M+, 2), 287 (M+, 4), 260 (64), 258 (bp) 240 (33).

Workup

  1. customPreparation
  2. customrecrystallized from ethanol/diethyl ether

Sources & evidence

ORD record
ord-df8fb63670654814b5c8b906a88afa37
Source dataset
uspto-grants-2009_08
Patent number
US07579474B2

Reaction notes

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