Hydrochloric Acid → N-{4-[4-(4-Oxo-piperidin-1-yl)-phenylsulfamoyl]-phenyl}-acetamide

HRID 1061337Notes

Reaction equation

HRID 1061337 reaction equation
O1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][S:18]([C:21]4[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:30])[CH3:29])=[CH:23][CH:22]=4)(=[O:20])=[O:19])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:4]CC1.Cl>[OH-].[Na+]>[O:4]=[C:5]1[CH2:6][CH2:7][N:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:30])[CH3:29])=[CH:23][CH:22]=3)(=[O:19])=[O:20])=[CH:13][CH:12]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22220392N-{4-[4-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-phenylsulfamoyl]-phenyl}-acetamide

Product 1

HCID 22220411N-{4-[4-(4-Oxo-piperidin-1-yl)-phenylsulfamoyl]-phenyl}-acetamideYield 60.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

N-{4-[4-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-phenylsulfamoyl]-phenyl}-acetamide (which was obtained in Example 215) (2.2 g, 5.1 mmol) was treated with concentrated hydrochloric acid (50 mL) at 0° C. and then allowed to warm to room temperature. After 30 min., 20 mL of 5 N NaOH was added dropwise and the precipitate was collected by filtration, and dried over P2O5 to give the title compound as a white solid (1.2 g); 1H NMR (300 MHz, DMSO-d6) δ 2.06 (s, 3H), 2.43 (t, J=5.8 Hz, 4H), 3.53 (t, J=5.8 Hz, 4H), 6.85-7.05 (m, 4H), 7.62 (d, J=9.0 Hz, 2H), 7.71 (d, J=9.0 Hz, 2H), 9.81 (s, 1H), 10.35 (s, 1H); MS (ES) m/z: 388.3 (MH+); HRMS Calcd. for C19H21N3O4S(M+):387.1253. Found: 387.1272.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-5f9bea53023d447194c99e9f04bc49c3
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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