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

반응식

HRID 566875 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d0c80c34be8242cfb1bf393155c62d2b
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06177422B1

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