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Potassium Carbonate → 4-(3-Methyl-5-nitro-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1993652
ノート
印刷プレビュー

反応式

HRID 1993652 の反応式
Cl[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O.O>CN(C=O)C>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:2]2[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 896482-Chloro-3-methyl-5-nitropyridineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 22728543Water ethylacetate

生成物 1

HCID 685370044-(3-Methyl-5-nitro-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester収率 85.2%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
80 °C

実験手順

Treat a slurry of 2-chloro-3-methyl-5-nitro-pyridine (27.00 g, 0.156 mol) and piperazine-1-carboxylic acid tert-butyl ester (32.03 g, 0.172 mol) in anhydrous DMF (270 mL) with K2CO3 (34.55 g, 0.250 mol), then heat the reaction mixture at 80° C. under N2 overnight. Pour the resulting reaction mixture into 1/1 EtOAc/H2O (3,000 mL), separate the layers, then extract the aqueous layer with EtOAc (1,000 mL). Wash the combined organics with saturated aq. sodium chloride (3×1,000 mL each), dry over MgSO4, filter, then concentrate under reduced pressure to give a yellow solid. Slurry the yellow solid in hexanes/EtOAc, then recover the resulting solid by vacuum filtration. Wash with hexanes and vacuum filter to give (42.84 g) of 4-(3-methyl-5-nitro-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester as a yellow solid. Concentrate the filtrate under reduced pressure to give a yellow solid. Slurry the yellow solid in hexanes, then recover the resulting solid by vacuum filtration, washing with hexane and drying under vacuum filtration to give an additional (5.38 g) of 4-(3-methyl-5-nitro-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester compound as a yellow solid (48.22 g, 95.9% yield). 1H NMR (400 MHz, CDCl3) δ 8.96 (d, 1H), 8.14 (d, 1H), 3.57 (m, 4H), 3.41 (m, 4H), 2.36 (s, 3H), 1.48 (s, 9H); TOF-MS [ES+, M+H] Obs. m/z 323.1723, Calc. m/z 323.1719; Anal. Calcd. For C15H22N4O4: C, 55.88; H, 6.87; N, 17.37. Found C, 55.94; H, 6.87; N, 17.14.

後処理

  1. additionPour
  2. customseparate the layers
  3. extractionextract the aqueous layer with EtOAc (1,000 mL)
  4. washWash the combined organics with saturated aq. sodium chloride (3×1,000 mL each)
  5. dry with materialdry over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. customto give a yellow solid
  9. customrecover the resulting solid
  10. filtrationby vacuum filtration
  11. washWash with hexanes and vacuum
  12. filtrationfilter

出典と根拠

ORDレコード
ord-c0b9b06d7fcc4e218d915df0e80a7947
出典データセット
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07652015B2

反応ノート

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