1-Methylpiperazine → HCID 86713635、化合物

HRID 1430481ノート

反応式

HRID 1430481 の反応式
Br[CH2:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[F:12].[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.CCN(C(C)C)C(C)C>C1COCC1>[F:12][C:4]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=1[CH2:2][N:17]1[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH2:16]1

参加物

5

反応物 3

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 103539672-(Bromomethyl)-1-fluoro-4-nitrobenzene

生成物 1

HCID 86713635HCID 86713635、化合物収率 70%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of ˜80% pure 2-(bromomethyl)-1-fluoro-4-nitrobenzene (0.956 g, 3.27 mmol) in THF (10 mL) was added slowly drop-wise to a −20° C. solution of 1-methylpiperazine (0.393 g, 3.92 mmol) and DIEA (1.142 mL, 6.54 mmol) in THF (20 mL), the mixture allowed to warm slowly to RT and stirred overnight. The resulting solid was removed via filtration and the filtrate was concentrated to dryness and purified via silica gel chromatography (EtOAc, MeOH/DCM) to afford 1-(2-fluoro-5-nitrobenzyl)-4-methylpiperazine (577 mg, 70% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.28 (dd, J=6.2, 3.0 Hz, 1H), 8.21 (ddd, J=9.0, 4.4, 3.0 Hz, 1H), 7.47 (t, J=9.1 Hz, 1H), 3.60 (s, 2H), 2.48-2.25 (br m, 8H), 2.14 (s, 3H); MS (ESI) m/z: 254.1 [M+H]+.

後処理

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

出典と根拠

ORDレコード
ord-34f0af4578b84d6ca39ecf6f2dd89080
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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