Hydrochloric Acid → 1-[3,5-Bis(trifluoromethyl)phenyl]ethan-1-amine--hydrogen chloride (1/1)

HRID 966968노트

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HRID 966968 반응식
[ClH:1].CO[NH2:4].[F:5][C:6]([F:21])([F:20])[C:7]1[CH:8]=[C:9]([C:17](=O)[CH3:18])[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1.C([O-])(=O)C.[Na+].[O-]S([O-])(=O)=O.[Mg+2].Cl>C(O)C.O>[ClH:1].[CH3:18][CH:17]([C:9]1[CH:8]=[C:7]([C:6]([F:21])([F:20])[F:5])[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=1)[NH2:4]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 1216161-(3,5-Bis(trifluoromethyl)phenyl)ethan-1-oneHCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochloride

생성물 1

HCID 222935631-[3,5-Bis(trifluoromethyl)phenyl]ethan-1-amine--hydrogen chloride (1/1)수율 100%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매2회

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온도
0 °C

실험 절차

O-Methylhydroxylamine hydrochloride (19.57 g, 234 mmol) was added to a solution of 1-[3,5-bis(trifluoromethyl)phenyl]ethanone (50 g, 195 mmol), and sodium acetate (31.9 g, 234 mmol) in ethanol (450 mL) and water (150 mL) and the mixture was heated under reflux for 18 hours. The mixture was cooled, water (1000 mL) was added and the mixture was extracted with diethyl ether. The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was dissolved in tetrahydrofuran (100 mL), cooled to 0° C. and borane-tetrahydrofuran complex (1M in tetrahydrofuran, 730 mL) was added. The mixture was heated under reflux for 18 hours, cooled and hydrochloric acid (5M, 500 mL) was added slowly. The tetrahydrofuran was evaporated under reduced pressure and the mixture was basified with aqueous sodium hydroxide (4M). The mixture was extracted with ether and the combined organic fractions were washed with aqueous sodium hydroxide (4M) and dried (MgSO4), and ethereal hydrogen chloride (400 mL, 400 mmol) was added. The solid was collected, washing with diethyl ether, and dried in vacuo to give (RS)-α-methyl-3,5-bis(trifluoromethyl)benzenemethanamine hydrochloride as a colorless solid (48.2 g, 100%). 1H NMR (400 MHz, CD3OD) δ 8.13 (2H, s), 8.07 (1H, s), 4.73 (1H, q, J 6.8 Hz), 3.31 (2H, d, J 1.4 Hz), and 1.69 (3H, d, J 6.8 Hz). m/z (ES+) 258 (M+1). A sample was suspended in aqueous sodium hydroxide (4M) and extracted with ether. The combined organic fractions were washed with aqueous sodium hydroxide (4M), dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.85 (2H, s), 7.76 (1H, s), 4.30 (1H, q, J 6.6 Hz), 1.74 (2H, br s), and 1.42 (3H, d, J 6.6 Hz). m/z (ES+) 258 (M+1).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. temperatureThe mixture was cooled
  4. extractionthe mixture was extracted with diethyl ether
  5. dry with materialThe combined organic fractions were dried (MgSO4)
  6. customthe solvent was evaporated under reduced pressure
  7. dissolutionThe residue was dissolved in tetrahydrofuran (100 mL)
  8. additionborane-tetrahydrofuran complex (1M in tetrahydrofuran, 730 mL) was added
  9. temperatureThe mixture was heated
  10. temperatureunder reflux for 18 hours
  11. temperaturecooled
  12. additionhydrochloric acid (5M, 500 mL) was added slowly
  13. customThe tetrahydrofuran was evaporated under reduced pressure
  14. extractionThe mixture was extracted with ether
  15. washthe combined organic fractions were washed with aqueous sodium hydroxide (4M)
  16. additionwas added
  17. customThe solid was collected
  18. washwashing with diethyl ether
  19. customdried in vacuo

출처 및 근거

ORD 기록
ord-817e8c3a320843ad97280bc88e6f81c9
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06953792B2

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