Sodium Hydroxide → 4-(Piperidine-1-sulfonyl)aniline

HRID 1787988Notes

Reaction equation

HRID 1787988 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=O)C.C(OCC)(=O)C.ClCCl.[OH-].[Na+]>Cl>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 79780N-(4-(1-Piperidinylsulfonyl)phenyl)acetamideHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 2366484-(Piperidine-1-sulfonyl)anilineYield 70.62%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

N-[4-(Acetylamino)phenylsulfonyl]piperidine (Example 5) was heated at 100° C. in 20% hydrochloric acid (5 mL) for one hour (TLC ethyl acetate/dichloromethane 8:2). The solution is neutralized at 0° C. with NaOH. The precipitate that forms is filtered and recrystallized from methanol/diethyl ether to afford the desired N-[4-(amino)phenylsulfonyl]piperidine. 70.62% yield; white solid.

Workup

  1. filtrationThe precipitate that forms is filtered
  2. customrecrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-72f5b3bac1774de1a6a19a42599f80db
Source dataset
uspto-grants-2009_03
Patent number
US07511133B2

Reaction notes

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