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

HRID 2421977노트

반응식

HRID 2421977 반응식
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

참가 물질

6

반응물 3

HCID 313Hydrochloric Acid3회HCID 887MethanolHCID 2796148Tert-butyl (1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)piperidin-4-yl)carbamate

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 312751,4-Dioxane용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-648562df9bf94f6da6f5cf8bf9cb6bf9
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960380B2

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