Hydrochloric Acid → 4-(4-Amino-piperidine-1-sulfonyl)-2-fluoro-N-phenethyl-benzamide

HRID 337219Notes

Reaction equation

HRID 337219 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23](=[O:33])[NH:24][CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[C:19]([F:34])[CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)(C)(C)C.Cl>O1CCOCC1>[NH2:7][CH:8]1[CH2:9][CH2:10][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([NH:24][CH2:25][CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[O:33])=[C:19]([F:34])[CH:18]=2)(=[O:15])=[O:16])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71060106[1-(3-Fluoro-4-phenethylcarbamoyl-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

Product 1

HCID 710600854-(4-Amino-piperidine-1-sulfonyl)-2-fluoro-N-phenethyl-benzamideYield 84.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

[1-(3-Fluoro-4-phenethylcarbamoyl-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (0.38 g, 0.7 mmol) was suspended in a 4M solution of HCl in Dioxane (5 ml). The resulting suspension was stirred at room temperature for 3 hours. After this time the solution was concentrated under vacuum, then azeotroped with methanol and suspended in diethyl ether. The resulting solid precipitate was then collected by filtration, washed with diethyl ether and dried under vacuum to afford the title compound (0.24 g, 80% yield) as a white solid. Tr=1.20 min, m/z (ES+) (M+H)+ 406.

Workup

  1. concentrationAfter this time the solution was concentrated under vacuum
  2. customazeotroped with methanol
  3. filtrationThe resulting solid precipitate was then collected by filtration
  4. washwashed with diethyl ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-4f6626aa05f84885b3b383fba2e3257b
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

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