Hydrochloric Acid → 4-Cbz-aminopiperidine

HRID 1841936Notes

Reaction equation

HRID 1841936 reaction equation
Cl.C(OC([N:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:11][CH2:10]1)=O)(C)(C)C>O1CCOCC1>[CH2:19]([O:18][C:16](=[O:17])[NH:15][CH:12]1[CH2:13][CH2:14][NH:9][CH2:10][CH2:11]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15143051-Boc-4-Cbz-amino-piperidine

Product 1

HCID 15143044-Cbz-aminopiperidineYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

HCl (10 ml, 4M solution in dioxane) was added in one portion to a stirred solution of 4-benzyloxycarbonylamino-piperidine-1-carboxylic acid tert-butyl ester (1.2 g, 3.6 mmol) in dioxane (5 ml) and the suspension was stirred at room temperature under a nitrogen atmosphere for 3 hours. After this time the reaction was concentrated under vacuum and the resulting solid was collected by filtration, washed with TBME (3×100 ml) and dried under vacuum to give the title compound (0.74 g, 88% yield) as a white solid. Tr=1.03 min m/z (ES+) (M+H+) 236.

Workup

  1. concentrationAfter this time the reaction was concentrated under vacuum
  2. filtrationthe resulting solid was collected by filtration
  3. washwashed with TBME (3×100 ml)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-f85007f957d844f1ac86da20b550d600
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

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