1-Methylpiperazine → 1-(3-Fluoro-5-nitrobenzyl)-4-methylpiperazine

HRID 1430546노트

반응식

HRID 1430546 반응식
Br[CH2:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([F:12])[CH:4]=1.CCN(C(C)C)C(C)C.[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>C1COCC1>[F:12][C:5]1[CH:4]=[C:3]([CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=1)[CH2:2][N:26]1[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]1

참가 물질

5

반응물 3

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 647705451-(Bromomethyl)-3-fluoro-5-nitrobenzene

생성물 1

HCID 867136821-(3-Fluoro-5-nitrobenzyl)-4-methylpiperazine수율 80%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A −20° C. solution of 1-(bromomethyl)-3-fluoro-5-nitrobenzene (0.95 g, 4.06 mmol) and DIEA (1.418 ml, 8.12 mmol) in THF (20 mL) was treated drop-wise with a solution of 1-methylpiperazine (0.488 g, 4.87 mmol) in THF (10 mL) and stirred at RT overnight as the cooling bath expired. The solid was removed via filtration and the filtrate concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford 1-(3-fluoro-5-nitrobenzyl)-4-methylpiperazine (820 mg, 80% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.01 (s, 1H), 7.97 (dt, J=8.6, 2.3 Hz, 1H), 7.64 (dd, J=9.2, 2.2 Hz, 1H), 3.60 (s, 2H), 2.41 (s, 8H), 2.21 (s, 3H); MS (ESI) m/z: 254.1 [M+H]+.

후처리

  1. customThe solid was removed via filtration
  2. concentrationthe filtrate concentrated to dryness
  3. custompurified via silica gel chromatography (MeOH/DCM)

출처 및 근거

ORD 기록
ord-b72f401c00a9416081746e28ee987eb6
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940756B2

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