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

HRID 717271Notes

Reaction equation

HRID 717271 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-7a40de0e1c6b4387a3bdf4af57b6084c
Source dataset
uspto-grants-2015_11
Patent number
US09193709B2

Reaction notes

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