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

HRID 539664Notes

Reaction equation

HRID 539664 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-39bee5a4a4244673ab6ca7a39c8c9cb7
Source dataset
uspto-grants-2014_10
Patent number
US08871766B2

Reaction notes

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