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

反応式

HRID 566875 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d0c80c34be8242cfb1bf393155c62d2b
出典データセット
uspto-grants-2001_01
特許番号
US06177422B1

関連ノート

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