Hydrochloric Acid → 3-(4-(2-Methoxyethoxy)piperidine-4-carboxamido)phenyl dimethylcarbamate

HRID 216066Notes

Reaction equation

HRID 216066 reaction equation
[CH3:1][N:2]([CH3:33])[C:3]([O:5][C:6]1[CH:7]=[C:8]([NH:12][C:13]([C:15]2([O:28][CH2:29][CH2:30][O:31][CH3:32])[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>[CH3:33][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([O:28][CH2:29][CH2:30][O:31][CH3:32])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[O:14])[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67036832Tert-butyl 4-(3-(dimethylcarbamoyloxy)phenylcarbamoyl)-4-(2-methoxyethoxy)piperidine-1-carboxylate

Product 1

HCID 670367663-(4-(2-Methoxyethoxy)piperidine-4-carboxamido)phenyl dimethylcarbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 4-(3-(dimethylcarbamoyloxy)phenylcarbamoyl)-4-(2-methoxyethoxy)piperidine-1-carboxylate from step C (2.1 g, 4.4 mmol) was treated with HCl (4.0 N in dioxane, 5.5 mL, 22 mmol) in methanol (20 mL) at 50° C. for 30 minutes. The mixture was concentrated to give the title compound as the hydrochloride salt in quantitative yield. MS (ES+) [M+H]+=380.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-44fae2fefce1411a97990eb72e704906
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

Loading…