Hydrochloric Acid → 4-(piperidin-4-yl)-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide

HRID 1876683Notes

Reaction equation

HRID 1876683 reaction equation
[S:1]1[C:5]([NH:6][S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:21][CH2:20][N:19](C(=O)C(F)(F)F)[CH2:18][CH2:17]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])=[N:4][CH:3]=[N:2]1.[OH-].[Na+].Cl>O>[NH:19]1[CH2:18][CH2:17][CH:16]([C:13]2[CH:14]=[CH:15][C:10]([S:7]([NH:6][C:5]3[S:1][N:2]=[CH:3][N:4]=3)(=[O:9])=[O:8])=[CH:11][CH:12]=2)[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59465762N-(1,2,4-thiadiazol-5-yl)-4-(1-(2,2,2-trifluoroacetyl)piperidin-4-yl)benzenesulfonamide

Product 1

HCID 594659034-(piperidin-4-yl)-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Prepared using general procedure 16. A mixture of N-(1,2,4-thiadiazol-5-yl)-4-(1-(2,2,2-trifluoroacetyl)piperidin-4-yl)benzenesulfonamide (2.0 g, 4.8 mmol), NaOH (1.92 g, 48.0 mmol), and H2O (25 mL) was stirred at RT for 30 minutes. An aqueous 1.0 N HCl solution was added (48.0 mL, 48 mmol), and the mixture was azeotroped with MeOH (3×100 mL). A 9:1 solution of CH2Cl2 and MeOH (100 mL) was added, and the mixture was filtered to remove NaCl. The filtrate was concentrated under reduced pressure to give 4-(piperidin-4-yl)-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide as a clear oil which solidified upon standing (1.5 g, 96%). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=325.3; tR=0.99 min.

Workup

  1. customPrepared
  2. customthe mixture was azeotroped with MeOH (3×100 mL)
  3. additionA 9:1 solution of CH2Cl2 and MeOH (100 mL) was added
  4. filtrationthe mixture was filtered
  5. customto remove NaCl
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0b09e57bc74f459a8aeaa26a306480a1
Source dataset
uspto-grants-2012_11
Patent number
US08309587B2

Reaction notes

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