1,4-Dioxane hydrochloride → cis(+/-)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride

HRID 43717

Reaction equation

HRID 43717 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][C@H:13]2[O:25][CH2:26][CH3:27])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].Cl.O1CCOCC1>C(O)C>[ClH:1].[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][NH:15][CH2:14][C@H:13]2[O:25][CH2:26][CH3:27])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86648478tert-Butyl cis(+/-)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidine-1-carboxylate

Product 1

HCID 86648665cis(+/-)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochlorideYield 231.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl cis(±)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidine-1-carboxylate obtained in Example (125a) (4.31 g, 10.8 mmol) was dissolved in ethanol (25 mL). A 4 N hydrochloric acid/dioxane solution (25 mL, 100 mmol) was added, and the mixture was stirred at room temperature for 1.5 hours. The reaction solution was concentrated under reduced pressure to obtain 4.22 g of the title compound as a pale pink amorphous solid (quant.).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9f1049aeb11f4cf6864006a2a1bc186c
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Linked notes

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