Hydrochloric Acid → 4-{1-(3,4-Dimethoxyphenoxy)-4-[8-(methylamino)-3-azabicyclo-[3.2.1]oct-3-yl]butyl}benzonitrile

HRID 411531노트

반응식

HRID 411531 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([O:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=2)[CH2:10][CH2:11][CH2:12][N:13]2[CH2:19][CH:18]3[CH:20]([N:21](C)[C:22](=O)[O:23]C(C)(C)C)[CH:15]([CH2:16][CH2:17]3)[CH2:14]2)=[CH:5][CH:4]=1)#[N:2].Cl>C(OCC)(=O)C>[OH-:23].[NH4+:2].[CH3:40][O:39][C:33]1[CH:32]=[C:31]([CH:36]=[CH:35][C:34]=1[O:37][CH3:38])[O:30][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=1)[CH2:10][CH2:11][CH2:12][N:13]1[CH2:19][CH:18]2[CH:20]([NH:21][CH3:22])[CH:15]([CH2:16][CH2:17]2)[CH2:14]1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 18540880Tert-butyl 3-[4-(4-cyanophenyl)-4-(3,4-dimethoxyphenoxy)butyl]-3-azabicyclo[3.2.1]oct-8-yl(methyl)carbamate

생성물 2

HCID 14923Ammonium HydroxideHCID 185409394-{1-(3,4-Dimethoxyphenoxy)-4-[8-(methylamino)-3-azabicyclo-[3.2.1]oct-3-yl]butyl}benzonitrile수율 120.8%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
25 °C

실험 절차

A suspension of tert-butyl 3-[4-(4-cyanophenyl)-4-(3,4-dimethoxyphenoxy)butyl]-3-azabicyclo[3.2.1]oct-8-yl(methyl)carbamate (see step (iv) above; 2.67 g, 4.86 mmol) in ethyl acetate saturated with HCl (60 mL) was stirred overnight at 25° C. under nitrogen. The mixture was partitioned with water (100 mL) and ethyl acetate (50 mL). The aqueous layer was washed with ethyl acetate (50 mL) before being separated, basified with saturated sodium bicarbonate (50 mL) and then extracted with dichloromethane (3×50 mL). The organic extracts were dried (Na2SO4), filtered, concentrated in vacuo and then chromatographed on silica gel, eluting with dichloromethane:methanol:concentrated ammonium hydroxide (92:7:1), to afford 1.32 g (61%) of the title compound as a yellow oil.

후처리

  1. customThe mixture was partitioned with water (100 mL) and ethyl acetate (50 mL)
  2. washThe aqueous layer was washed with ethyl acetate (50 mL)
  3. custombefore being separated
  4. extractionextracted with dichloromethane (3×50 mL)
  5. dry with materialThe organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customchromatographed on silica gel
  9. washeluting with dichloromethane

출처 및 근거

ORD 기록
ord-fd5eaa59aa07495792cae7183a5d8028
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559162B2

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