Hydrochloric Acid → N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-2-oxo-1-(4-piperidinyl)-4-imidazolidinecarboxamide hydrochloride

HRID 2080964Notes

Reaction equation

HRID 2080964 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][NH:13][C:14]([CH:16]1[CH2:20][N:19]([CH:21]2[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]2)[C:18](=[O:34])[N:17]1[CH3:35])=[O:15].Cl>O1CCOCC1>[ClH:1].[Cl:1][C:2]1[C:7]([C:8]([F:9])([F:11])[F:10])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][NH:13][C:14]([CH:16]1[CH2:20][N:19]([CH:21]2[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]2)[C:18](=[O:34])[N:17]1[CH3:35])=[O:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 671035531,1-Dimethylethyl 4-{4-[({[2-chloro-3-(trifluoromethyl)phenyl]methyl}amino)carbonyl]-3-methyl-2-oxo-1-imidazolidinyl}-1-piperidinecarboxylate

Product 1

HCID 67103577N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-2-oxo-1-(4-piperidinyl)-4-imidazolidinecarboxamide hydrochlorideYield 160%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 1,1-dimethylethyl 4-{4-[({[2-chloro-3-(trifluoromethyl)phenyl]methyl}amino)carbonyl]-3-methyl-2-oxo-1-imidazolidinyl}-1-piperidinecarboxylate (218 mg, 0.42 mmol) in 1,4-dioxane (3 ml) was treated with 4M hydrogen chloride in 1,4-dioxane (1 ml) and the reaction was stirred at room temperature for 4 hours. The solvent was evaporated and the gum was dissolved in methanol and the solvent evaporated. The residue was triturated with ether and the solid was collected and dried to give N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-2-oxo-1-(4-piperidinyl)-4-imidazolidinecarboxamide hydrochloride (153 mg, 80%), LC/MS [M+H]+=419, retention time=1.75 minutes.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe gum was dissolved in methanol
  3. customthe solvent evaporated
  4. customThe residue was triturated with ether
  5. customthe solid was collected
  6. customdried

Sources & evidence

ORD record
ord-ea2cf188e1fb485293288c8594545ada
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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