4-(4-Benzoylpiperazin-1-yl)-2-nitrobenzoic acid → HCID 67185182、化合物

HRID 1966457ノート

反応式

HRID 1966457 の反応式
[C:1]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[C:17]([N+:24]([O-])=O)[CH:16]=2)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.C1COCC1.[Pt]=O>[NH2:24][C:17]1[CH:16]=[C:15]([N:12]2[CH2:11][CH2:10][N:9]([C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:14][CH2:13]2)[CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=[O:20]

参加物

5

反応物 1

HCID 584256644-(4-Benzoylpiperazin-1-yl)-2-nitrobenzoic acid

生成物 1

HCID 67185182HCID 67185182、化合物収率 70%

試薬・触媒・溶媒 3

HCID 82844Platinum oxide (PtO)触媒HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

The obtained 4-(4-benzoylpiperazin-1-yl)-2-nitrobenzoic acid (0.40 g, 93%) was dissolved in 30 ml ethanol and 10 ml THF, followed by the addition of platinum oxide (20 mg, 5%) and stirred under hydrogen gas for 16 hours. The reaction was filtered with the aid of celite. 2-amino-4-(4-bezoylpiperazin-1-yl)benzoic acid (0.24 g, 70%) was obtained after removing of solvents. To a solution of 2-amino-4-(4-bezoylpiperazin-1-yl)benzoic acid (0.2 g, 0.6 mmol) and benzaldehyde (0.14 ml, 1.3 mmol) added sodium triacetoxyborohydride (0.4 g, 1.8 mmol) and stirred under argon atmosphere overnight. The reaction was quenched with 10 ml water and extracted with ethyl acetate (3×20 ml), followed by drying it over anhydrous sodium sulfate. 2-(benzylamino)-4-(4-benzoylpiperazin-1-yl)benzoic acid (0.11 g, 40%) was obtained after concentration. 1H NMR (500 MHz, CDCl3) δ (ppm) 3.25-3.88 (m, br, 8H), 4.48 (s, 2H), 6.20 (d, J=2.3 Hz, 1H), 6.22 (dd, J=2.3, 9.1 Hz, 1H), 7.30-7.45 (m, 10H), 7.48 (d, J=9.1 Hz, 1H), 8.25 (s, 1H), 10.65 (s, 1H).

後処理

  1. filtrationThe reaction was filtered with the aid of celite

出典と根拠

ORDレコード
ord-593f55e1c22d4acb932d4c9e8edf2689
出典データセット
uspto-grants-2013_04
特許番号
US08420640B2

反応ノート

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