Water → 1-Methyl-3-hydroxymethyl-4-(3,4-dichlorophenyl)piperidine

HRID 843265Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[CH:4]([C:16](OC)=[O:17])[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[CH:4]([CH2:16][OH:17])[CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-methyl-3-methoxycarbonyl-4-(3,4-dichlorophenyl)piperidine (10 g, 33 mmol) in tetrahydrofuran (100 mL) at −20° C. was added a suspension of lithium aluminium hydride (1.2 g, 32 mmol) in tetrahydrofuran (150 mL) over 35 min. The reaction was heated to 0° C. followed by successive addition of water (1 mL), sodium hydroxide (4 N, 1 mL) and water (10 mL). The reaction was stirred for another 30 min and filtered through celite. Evaporation of the solvent afforded 9.3 g of the title compound as an oil.

Workup

filtrationfiltered through celite
customEvaporation of the solvent

Sources & evidence

ORD record: ord-1d1bee61e7124a77a0178d1ef0ade9e5
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06376673B1

Reaction notes

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