Ammonia methanol → Benzyl cis(+/-)-(1-carbamothioyl-3-methoxypiperidin-4-yl)-carbamate

HRID 43513Notes

Reaction equation

HRID 43513 reaction equation
[N:1]1([C:6]([N:8]2[CH2:13][CH2:12][C@H:11]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C@H:10]([O:25][CH3:26])[CH2:9]2)=[S:7])C=CN=C1.N.CO>C1COCC1.[Cl-].[Na+].O>[C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@H:10]([O:25][CH3:26])[CH2:9]1)(=[S:7])[NH2:1]

Participants

5

Reactant 2

HCID 21705897Ammonia methanolHCID 86648520Benzyl cis(+/-)-[1-(1H-imidazol-1-ylcarbonothioyl)-3-methoxypiperidin-4-yl]-carbamate

Product 1

HCID 86648521Benzyl cis(+/-)-(1-carbamothioyl-3-methoxypiperidin-4-yl)-carbamateYield 67.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Benzyl cis(±)-[1-(1H-imidazol-1-ylthiocarbonyl)-3-methoxypiperidin-4-yl]-carbamate obtained in Example (64a) (about 1.36 mmol) was dissolved in THF (2 mL). A 2 N ammonia/methanol solution (10 mL) was added, and the mixture was stirred for 42 hours. Brine was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The precipitated solid was collected by filtration to obtain 296.5 mg of the title compound as a white solid (67%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-413e645128ff40229443a53d13eb9b8f
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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