Water → Tert-butyl 4-(3-(5-chloro-2-methyl-4-nitrophenoxy)propyl)piperazine-1-carboxylate

HRID 415065

反応式

HRID 415065 の反応式
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.[H-].[Na+].[Cl:20][C:21]1[CH:26]=[C:25](F)[C:24]([CH3:28])=[CH:23][C:22]=1[N+:29]([O-:31])=[O:30].O>C1COCC1>[Cl:20][C:21]1[C:22]([N+:29]([O-:31])=[O:30])=[CH:23][C:24]([CH3:28])=[C:25]([CH:26]=1)[O:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydride2 回HCID 875934-Chloro-2-fluoro-5-nitrotolueneHCID 162178001-Boc-4-(3-hydroxypropyl)piperazine

生成物 1

HCID 59349539Tert-butyl 4-(3-(5-chloro-2-methyl-4-nitrophenoxy)propyl)piperazine-1-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
65 °C

実験手順

A flask was charged with tert-butyl 4-(3-hydroxypropyl)piperazine-1-carboxylate (905 mg, 3.7 mmol, commercially available from Alrich), sodium hydride, 95% (24 mg, 4.6 mmol) and THF (10 mL), and the mixture was stirred under N2 for 15 minutes, after which time a solution of 1-chloro-5-fluoro-4-methyl-2-nitrobenzene (700 mg, 3.7 mmol, commercially available from Aldrich) in THF (10 mL) was added to the sodium hydride mixture at 0° C. The reaction mixture was heated to 65° C. for 15 hours. Water was added to the cooled reaction mixture and the mixture was extracted with ethyl acetate. The organic solvent was concentrated under reduced pressure and the resulting solid was purified by silica column chromatography eluting with 5% methanol in dichloromethane, to give 1.2 g (78 5 yield) of tert-butyl 4-(3-(5-chloro-2-methyl-4-nitrophenoxy) propyl)piperazine-1-carboxylate. 1H-NMR (400 MHz, CDCl3) δ 7.82 (s, 1H), 6.92 (s, 1H), 3.92 (t, 2H), 3.06 (m, 4H), 2.62 (m, 4H), 2.36 (m, 2H), 2.34 (s, 3H), 1.84 (m, 2H), 1.42 (s, 9H). MS (EI): 414 (MH+).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationThe organic solvent was concentrated under reduced pressure
  3. customthe resulting solid was purified by silica column chromatography
  4. washeluting with 5% methanol in dichloromethane

出典と根拠

ORDレコード
ord-f13a68e64914483aa4daceb4a842ffb4
出典データセット
uspto-grants-2012_01
特許番号
US08088767B2

関連ノート

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