1,4-Dioxane hydrochloride → 4-(4-Cyanobenzyl)-4-hydroxypiperidine hydrochloride

HRID 240377Notes

Reaction equation

HRID 240377 reaction equation
[C:1]([C:3]1[CH:23]=[CH:22][C:6]([CH2:7][C:8]2([OH:21])[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[CH:5][CH:4]=1)#[N:2].[ClH:24].O1CCOCC1>O1CCOCC1>[ClH:24].[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C:8]2([OH:21])[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[CH:22][CH:23]=1)#[N:2]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 70851493Tert-butyl 4-(4-cyanobenzyl)-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 866808464-(4-Cyanobenzyl)-4-hydroxypiperidine hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 4-(4-cyanobenzyl)-4-hydroxypiperidine-1-carboxylate (19 g) in 1,4-dioxane (50 mL) was added 4.0 M HCl/1,4-dioxane solution (76 mL) at 0° C., and the mixture was stirred at room temperature for 10 hr. The resulting solid was collected by filtration, washed with ethyl acetate (100 mL) and diethyl ether (200 mL), and dried under reduced pressure to give the title compound (9.3 g).

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with ethyl acetate (100 mL) and diethyl ether (200 mL)
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-5a21e37617314208ad2e05e977d780aa
Source dataset
uspto-grants-2014_02
Patent number
US08648079B2

Reaction notes

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