Hydrochloric Acid → 4-(Piperidin-4-yloxy)benzonitrile hydrochloride

HRID 529977

Reaction equation

HRID 529977 reaction equation
[ClH:1].C(OC([N:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)=O)(C)(C)C>>[ClH:1].[NH:9]1[CH2:10][CH2:11][CH:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=2)[CH2:13][CH2:14]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 23019443tert-Butyl 4-(4-cyanophenoxy)piperidine-1-carboxylate

Product 1

HCID 178322734-(Piperidin-4-yloxy)benzonitrile hydrochloride

Procedure

Step-2: To a stirred solution of 100 mL (400 mmol) of 4N HCl in dioxanes was added the step-1 product, 4-(4-cyanophenoxy)piperidine-1-carboxylic acid tert-butyl ester, (12.60 g, 0.0417 mol) and the mixture stirred 2 h, and 150 mL of 67% Et2O/hexanes added. The resulting slurry was filtered and dried under vacuum (1 torr, 60° C.) to afford the step-2 product, 4-(piperidin-4-yloxy)benzonitrile hydrochloride, as a white solid (9.10 g, 91%): LCMS [MH+]203, Rt 1.23.

Workup

  1. filtrationThe resulting slurry was filtered
  2. customdried under vacuum (1 torr, 60° C.)

Sources & evidence

ORD record
ord-851b7cf77c524bbcb0172d2e5ec6cba4
Source dataset
uspto-grants-2016_05
Patent number
US09351964B2

Linked notes

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