Hydrochloric Acid → 1-(4-Nitrobenzenesulfonyl)piperidin-4-amine

HRID 337199Notes

Reaction equation

HRID 337199 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]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)(C)(C)C.Cl>O1CCOCC1>[N+:23]([C:20]1[CH:19]=[CH:18][C:17]([S:14]([N:11]2[CH2:10][CH2:9][CH:8]([NH2:7])[CH2:13][CH2:12]2)(=[O:15])=[O:16])=[CH:22][CH:21]=1)([O-:25])=[O:24]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71079538[1-(4-Nitro-benzenesulfonyl)-piperidin-4-yl]carbamic acid tert-butyl ester

Product 1

HCID 284183251-(4-Nitrobenzenesulfonyl)piperidin-4-amineYield 89.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

[1-(4-Nitro-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (3.5 g, 9.0 mmol) was suspended in a 4M solution of HCl in Dioxane (100 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 (2.3 g, 86% yield) as a white solid. Tr=1.10 min, m/z (ES+) (M+H)+ 286.

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-9ddad51d7ab041b893c69633222a2db4
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

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