Hydrochloric Acid → Benzyl cis(+/-)-[1-(1H-imidazol-1-ylcarbonothioyl)-3-methoxypiperidin-4-yl]-carbamate

HRID 43512

Reaction equation

HRID 43512 reaction equation
[CH3:1][O:2][C@H:3]1[C@@H:8]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][CH2:6][NH:5][CH2:4]1.[C:20](N1C=CN=C1)([N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1)=[S:21].Cl>C1COCC1>[N:22]1([C:20]([N:5]2[CH2:6][CH2:7][C@H:8]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C@H:3]([O:2][CH3:1])[CH2:4]2)=[S:21])[CH:26]=[CH:25][N:24]=[CH:23]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 802641,1'-ThiocarbonyldiimidazoleHCID 86648490Benzyl cis(+/-)-[3-methoxypiperidin-4-yl]carbamate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyl cis(±)-4-(3-methoxypiperidin-4-yl)-carbamate obtained by the method described in Example (40b) (735 mg, 1.37 mmol) was dissolved in THF (8 mL). 1,1′-Thiocarbonyldiimidazole (270 mg, 1.36 mmol) was added, and the mixture was stirred for 1.5 hours. 0.5 M hydrochloric acid was added to the reaction solution, followed by extraction with ethyl acetate and dichloromethane. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting compound was used for the next reaction without purification.

Workup

  1. extractionfollowed by extraction with ethyl acetate and dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting compound was used for the next reaction without purification

Sources & evidence

ORD record
ord-29d69e4f601b4ecbbaee4f6addca5f23
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Linked notes

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