4-(Piperazin-1-yl)benzene-1-sulfonamide → 4-[4-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-piperazin-1-yl]-benzenesulfonamide

HRID 566875

Reaction equation

HRID 566875 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[O:15]=[C:16]1[NH:21][C:20]2[CH:22]=[C:23]([CH:26]=O)[CH:24]=[CH:25][C:19]=2[O:18][CH2:17]1.[N:28]1([C:34]2[CH:39]=[CH:38][C:37]([S:40]([NH2:43])(=[O:42])=[O:41])=[CH:36][CH:35]=2)[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>C1COCC1>[O:15]=[C:16]1[NH:21][C:20]2[CH:22]=[C:23]([CH2:26][N:31]3[CH2:32][CH2:33][N:28]([C:34]4[CH:39]=[CH:38][C:37]([S:40]([NH2:43])(=[O:42])=[O:41])=[CH:36][CH:35]=4)[CH2:29][CH2:30]3)[CH:24]=[CH:25][C:19]=2[O:18][CH2:17]1

Participants

5

Reactant 3

HCID 9018974-(Piperazin-1-yl)benzene-1-sulfonamideHCID 5049666Sodium triacetoxyborohydrideHCID 107736383-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbaldehyde

Product 1

HCID 212639034-[4-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-piperazin-1-yl]-benzenesulfonamideYield 4.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium triacetoxyborohydride (1.2 g, 5.9 mmol) is added to a solution of 3-oxo-3,4-dihydro-2H-benzo[1,4]-oxazine-6-carbaldehyde (0.5 g, 2.8 mmol) and 4-(piperazin-1-yl)-benzenesulfonamide (0.17 g, 3.1 mmol) in 20 mL of THF. The mixture is stirred at room temperature overnight. The reaction is quenched by addition of 50 mL of water, and the THF is removed under reduced pressure. The precipitate is collected by filtration and recrystallized from methanol to give 0.05 g (4% yield) of 4-[4-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-piperazin-1-yl]-benzenesulfonamide; mp 150-153° C.

Workup

  1. customThe reaction is quenched by addition of 50 mL of water
  2. customthe THF is removed under reduced pressure
  3. filtrationThe precipitate is collected by filtration
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-d0c80c34be8242cfb1bf393155c62d2b
Source dataset
uspto-grants-2001_01
Patent number
US06177422B1

Linked notes

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