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

HRID 1430546ノート

反応式

HRID 1430546 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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]+.

後処理

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

出典と根拠

ORDレコード
ord-b72f401c00a9416081746e28ee987eb6
出典データセット
uspto-grants-2015_01
特許番号
US08940756B2

反応ノート

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