Hydrochloric Acid → 4-(piperidin-4-yl)-N-(pyrimidin-4-yl)benzenesulfonamide

HRID 1715929Notes

Reaction equation

HRID 1715929 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]3[CH2:22][CH2:21][N:20](C(=O)C(F)(F)F)[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[N:3][CH:2]=1.[OH-].[Na+].Cl>O>[NH:20]1[CH2:19][CH2:18][CH:17]([C:14]2[CH:13]=[CH:12][C:11]([S:8]([NH:7][C:4]3[CH:5]=[CH:6][N:1]=[CH:2][N:3]=3)(=[O:9])=[O:10])=[CH:16][CH:15]=2)[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59465873N-(pyrimidin-4-yl)-4-(1-(2,2,2-trifluoroacetyl)piperidin-4-yl)benzenesulfonamide

Product 1

HCID 594656714-(piperidin-4-yl)-N-(pyrimidin-4-yl)benzenesulfonamideYield 106.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Prepared using general procedure 16. A mixture of N-(pyrimidin-4-yl)-4-(1-(2,2,2-trifluoroacetyl)piperidin-4-yl)benzenesulfonamide (850 mg, 2.1 mmol), NaOH (412 mg, 10.3 mmol), and H2O (3 mL) was stirred at RT for 30 minutes. A 1.0 N aqueous HCl solution was added (10.3 mL, 10.3 mmol), and the mixture was azeotroped with MeOH (3×50 mL). A 1:1 solution of CH2Cl2 and MeOH (10 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-(pyrimidin-4-yl)benzenesulfonamide as a light yellow solid (710 mg). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=319.1; tR=0.43 min.

Workup

  1. customPrepared
  2. customthe mixture was azeotroped with MeOH (3×50 mL)
  3. additionA 1:1 solution of CH2Cl2 and MeOH (10 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-4a844b317d9a46cc82cb0b903152107f
Source dataset
uspto-grants-2010_09
Patent number
US07799822B2

Reaction notes

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