Water → [4-[3-(Benzylamino)-4-nitrophenyl]piperazin-1-yl]-phenylmethanone

HRID 1966427

반응식

HRID 1966427 반응식
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13](Br)[CH:12]=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]1([C:25]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN1C(=O)CCC1>[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([N:30]2[CH2:31][CH2:32][N:27]([C:25]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[O:26])[CH2:28][CH2:29]2)[CH:12]=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 7626541-BenzoylpiperazineHCID 24902978N-benzyl-5-bromo-2-nitroaniline

생성물 1

HCID 2906315[4-[3-(Benzylamino)-4-nitrophenyl]piperazin-1-yl]-phenylmethanone수율 1,362.5%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

A solution of N-benzyl-5-bromo-2-nitrobenzenamine (50 mg, 0.16 mmol) and phenyl(piperazin-1-yl)methanone (93 mg, 0.48 mmol) in NMP (1 mL) was heated to 110° C. for 16 h. The solution was cooled to room temperature to which was slowly added H2O (5 mL). The resulting yellow precipitate was filtered, washed with 2 mL of water, dried (high vacuum, 14 h) to furnish (4-(3-(benzylamino)-4-nitrophenyl)piperazin-1-yl)(phenyl)methanone (520 mg, 2.18 mmol), 92% yield. 1H NMR (500 MHz, CDCl3) d (ppm) 8.85 (m, 1H), 8.14 (d, J=9.5 Hz, 1H), 7.51-7.3 (m, 10H), 6.24 (dd, J=2.5 Hz, 10 Hz, 1H), 5.88 (d, J=2.5 Hz, 1H), 4.55 (d, J=5 Hz, 2H) 3.9-3.2 (m, 8H).+ESI HRMS (calcd for C24H24N4O3Na, M+Na) 439.1746, found 439.1741

후처리

  1. filtrationThe resulting yellow precipitate was filtered
  2. washwashed with 2 mL of water
  3. customdried (high vacuum, 14 h)

출처 및 근거

ORD 기록
ord-6a1dff251f6342e4a63d7807772b5687
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420640B2

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