Hydrochloric Acid → 1-[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]piperidin-4-amine

HRID 2421977ノート

反応式

HRID 2421977 の反応式
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)(C)(C)C.CO.Cl>C1COCC1.O1CCOCC1>[Cl:20][C:19]1[C:14]([N:11]2[CH2:10][CH2:9][CH:8]([NH2:7])[CH2:13][CH2:12]2)=[N:15][CH:16]=[C:17]([C:21]([F:23])([F:24])[F:22])[CH:18]=1

参加物

6

反応物 3

HCID 313Hydrochloric Acid3 回HCID 887MethanolHCID 2796148Tert-butyl (1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)piperidin-4-yl)carbamate

生成物 1

HCID 27961851-[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]piperidin-4-amine収率 128.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 312751,4-Dioxane溶媒3 回

実験手順

tert-Butyl{1-[3-chloro-5-(trifluoromethyl)pyridine-2-yl]piperidin-4-yl}carbamate (2.5 g, 6.4 mmol) was stirred in a mixture of THF (25 ml), MeOH (5 ml) and HCl in dioxane (4M, 6.5 ml) over night at rt. HCl in dioxane (4M, 4 ml) was added and after 4 h a third portion of HCl in dioxane/4M, 4 ml) was added. Stirring was continued for 48 h at rt. The solvent was evaporated, and the residue was dissolved in EtOAc. The resulting mixture was washed with aqueous saturated Na2CO3, water and dried over Na2SO4. Concentration of the organic phase yielded the title compound (2.3 g, 128%), which contained some impurities. 1H NMR (500 MHz, CDCl3): δ 1.50-1.54 (m, 2H), 1.88-1.94 (m, 2H), 2.93-3.00 (m, 3H), 4.01-4.04 (m, 2H), 7.74 (s, 1H), 8.38 (s, 1H); Mass Spectrum: M+H+ 280.

後処理

  1. additionwas added
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in EtOAc
  4. washThe resulting mixture was washed with aqueous saturated Na2CO3, water
  5. dry with materialdried over Na2SO4

出典と根拠

ORDレコード
ord-648562df9bf94f6da6f5cf8bf9cb6bf9
出典データセット
uspto-grants-2011_06
特許番号
US07960380B2

反応ノート

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