Piperazine → 1-((2-Chloro-6-fluorophenyl)methyl)piperazine

HRID 1406629

반응식

HRID 1406629 반응식
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH2:4]Cl.[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>C1COCC1>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH2:4][N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1

참가 물질

4

반응물 2

HCID 4837PiperazineHCID 1086751-Chloro-2-(chloromethyl)-3-fluorobenzene

생성물 1

HCID 7357371-((2-Chloro-6-fluorophenyl)methyl)piperazine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Synthesized according to General Procedure A: 2-chloro-6-fluorobenzyl chloride (4{7}, 5 mL, 39.1 mmol, 1 equiv.), piperazine (20.2 g, 234.8 mmol, 6 equiv.), THF (85.4 mL). Purification with flash column chromatography on silica gel (4:1 EtOAc:MeOH) afforded 5{7} (6.92 g, 77%) as a white solid. 1H-NMR (400 MHz, CDCl3): δ 7.14-7.08 (m, 2H), 6.94-6.86 (m, 1H), 3.62 (d, 2H, J=2.0 Hz), 2.78 (t, 4H, J=4.8 Hz), 2.44 (br s, 4H), 1.40 (br s, 1H). 13C-NMR (100 MHz, CDCl3): δ 161.8 (d, JC-F=247.5 Hz), 136.4 (d, JC-F=6.0 Hz), 128.8 (d, JC-F=9.6 Hz), 125.2, 123.6 (d, JC-F=18.0 Hz), 113.7 (d, JC-F=23.3 Hz), 54.0, 52.8, 45.9.

후처리

  1. customSynthesized
  2. customPurification with flash column chromatography on silica gel (4:1 EtOAc:MeOH)
  3. customafforded 5{7} (6.92 g, 77%) as a white solid

출처 및 근거

ORD 기록
ord-bfb40788a1a3466cae5545a80e6ba8a6
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916705B2

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