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

HRID 1424984Notes

Reaction equation

HRID 1424984 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-7a35a925304e45849dc88bf6112b2127
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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