2-Amino-1-[4-(3,4-dichlorophenoxy)-piperidine-1-yl]-3-methyl-butan-1-one → 1-[4-(3,4-Dichlorophenoxy)-piperidin-1-ylmethyl]-2-methyl-propylamine

HRID 496883Notes

Reaction equation

[NH2:1][CH:2]([CH:20]([CH3:22])[CH3:21])[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[CH2:7][CH2:6]1)=O>C1COCC1>[Cl:19][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[Cl:18])[O:11][CH:8]1[CH2:7][CH2:6][N:5]([CH2:3][CH:2]([NH2:1])[CH:20]([CH3:21])[CH3:22])[CH2:10][CH2:9]1

Participants

Conditions

Temperature: 70 °C

Procedure

The product of step (ii) (1.12 g) was dissolved in THF (10 ml) and Borane/THF complex (22.7 ml) added. The mixture was heated under reflux for 2 hours and cooled. The solvent was evaporated, the product dissolved in methanol (5 ml) and 50% aqueous HCl solution added. The mixture was heated to 70° C. for 1 hour and cooled to room temperature. The solvent was removed, ethyl acetate and 2N aqueous NaOH solution were added to give pH 9.0. The organic phase was separated and the solvent evaporated to give the sub-titled compound as an oil (0.98 g) which used without further purification.

Workup

additionBorane/THF complex (22.7 ml) added
temperatureThe mixture was heated
temperatureunder reflux for 2 hours
temperaturecooled
customThe solvent was evaporated
dissolutionthe product dissolved in methanol (5 ml)
addition50% aqueous HCl solution added
temperaturecooled to room temperature
customThe solvent was removed
additionethyl acetate and 2N aqueous NaOH solution were added
customto give pH 9.0
customThe organic phase was separated
customthe solvent evaporated

Sources & evidence

ORD record: ord-3ca421c901c242289dc465b17f7c8c6f
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06946478B2

Reaction notes

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