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

HRID 60577Notes

Reaction equation

HRID 60577 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-5051bbcc4bf84d07ac2ea7f3e4f899c7
Source dataset
uspto-grants-2016_09
Patent number
US09440990B2

Reaction notes

Loading…