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

HRID 216049Notes

Reaction equation

HRID 216049 reaction equation
[CH3:1][N:2]([CH3:29])[C:3]([O:5][C:6]1[CH:7]=[C:8]([NH:12][C:13]([C:15]2([CH3:28])[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)=[O:14])[CH:9]=[CH:10][CH:11]=1)=[O:4].Cl>CO>[CH3:29][N:2]([CH3:1])[C:3](=[O:4])[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]([C:15]2([CH3:28])[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]2)=[O:14])[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67037209Tert-butyl 4-(3-(dimethylcarbamoyloxy)phenylcarbamoyl)-4-methylpiperidine-1-carboxylate

Product 1

HCID 670367863-(4-Methylpiperidine-4-carboxamido)phenyl dimethylcarbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 4-(3-(dimethylcarbamoyloxy)phenylcarbamoyl)-4-methylpiperidine-1-carboxylate from step A (56 mgs, 0.138 mmol) was treated with HCl (4.0 N in dioxane, 0.17 mL, 0.69 mmol) in methanol (2.0 mL) at 40° C. for 3 hours. The mixture was concentrated to give the title compound as the hydrochloride salt in quantitative yield. MS (ES+) [M+H]+=306.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-466bb92e271847f688333a0050d066d6
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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