Hydrochloric Acid → (4-{[4-(Trifluoromethyl)phenyl]thio}cyclohexyl)amine

HRID 2421995

반응식

HRID 2421995 반응식
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:8]=[CH:7][C:6]([S:9][CH:10]2[CH2:15][CH2:14][CH:13]([NH:16]C(=O)OC(C)(C)C)[CH2:12][CH2:11]2)=[CH:5][CH:4]=1.Cl>C1COCC1.CO.O1CCOCC1>[F:25][C:2]([F:1])([F:24])[C:3]1[CH:4]=[CH:5][C:6]([S:9][CH:10]2[CH2:11][CH2:12][CH:13]([NH2:16])[CH2:14][CH2:15]2)=[CH:7][CH:8]=1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 86625880tert-Butyl (4-{[4-(trifluoromethyl)phenyl]thio}cyclohexyl)carbamate

생성물 1

HCID 67242225(4-{[4-(Trifluoromethyl)phenyl]thio}cyclohexyl)amine수율 97.1%

시약·촉매·용매 2

HCID 312751,4-Dioxane용매HCID 21899815MeOH tetrahydrofuran용매

실험 절차

tert-Butyl (4-{[4-(trifluoromethyl)phenyl]thio}cyclohexyl)carbamate (0.38 g, 1.01 mmol) was dissolved in THF:MeOH 8:2 (10 ml) and HCl in 1,4-dioxane (4M, 2 ml) was added. The reaction mixture was stirred at rt for 15 h, and then evaporated. The crude product was diluted with EtOAc (100 ml), washed with a mixture of saturated aqueous Na2CO3 and water (1:2, 100 ml) and water (2×100 ml). The organic layer was dried over Na2SO4, filtrated and evaporated to yield the title compound (0.27 g, 97%) as a 50:50 mixture of cis and trans isomers. 1H-NMR (CDCl3, 500 MHz): δ 7.56-7.48 (m, 4H), 7.46-7.39 (m, 4H), 3.59-3.52 (m, 1H), 3.17-3.07 (m, 1H), 2.90-2.79 (m, 1H), 2.78-2.68 (m, 1H), 2.13-2.03 (m, 2H), 1.99-1.14 (m, 18H); 13C-NMR (CDCl3, 125 MHz): δ 141.6, 141.0, 130.2, 129.7, 125.9, 125.9, 50.0, 48.9, 45.0, 44.0, 36.6, 32.3, 32.1, 30.5, 29.2, 29.0, 28.6.

후처리

  1. customevaporated
  2. additionThe crude product was diluted with EtOAc (100 ml)
  3. washwashed with a mixture of saturated aqueous Na2CO3 and water (1:2, 100 ml) and water (2×100 ml)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltrated
  6. customevaporated

출처 및 근거

ORD 기록
ord-0d101623b2354a80a2c589dc83e0d74b
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960380B2

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