Hydrochloric Acid → 3-(4-Aminopiperidine-4-carboxamido)phenyl dimethylcarbamate

HRID 216091Notes

Reaction equation

HRID 216091 reaction equation
C(OC([NH:8][C:9]1([C:22](=[O:36])[NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31](=[O:35])[N:32]([CH3:34])[CH3:33])[CH:25]=2)[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]1)=O)(C)(C)C.Cl.Cl.O1CCOCC1>CO>[CH3:33][N:32]([CH3:34])[C:31](=[O:35])[O:30][C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([NH:23][C:22]([C:9]2([NH2:8])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[O:36])[CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 204431481,4-Dioxane hydrochlorideHCID 68992221Tert-butyl 4-(tert-butoxycarbonylamino)-4-(3-(dimethylcarbamoyloxy)phenylcarbamoyl)piperidine-1-carboxylate

Product 1

HCID 670367823-(4-Aminopiperidine-4-carboxamido)phenyl dimethylcarbamateYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-(tert-butoxycarbonylamino)-4-(3-(dimethylcarbamoyloxy)phenylcarbamoyl)piperidine-1-carboxylate from step A (0.141 g, 0.28 mmol) in MeOH (2 mL) was added HCl (4 N in dioxane, 0.21 mL, 0.84 mmol). The mixture was stirred at room temperature for 14 hours. Further eqivalents of HCl/dioxane were added at this time, and the mixture stirred for a further 24 hours at room temperature. The solvent was removed under vacuum to afford the title compound (0.084 g, 98%), which was carried on crude. MS (ES+) [M+H]+=307.

Workup

  1. stirringthe mixture stirred for a further 24 hours at room temperature
  2. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-6d2431fc81144474b28e5057190996f2
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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