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Hydrochloric Acid → 4-({3-[8-(Methylamino)-3-azabicyclo[3.2.1]oct-3-yl]propyl}amino)benzonitrile

HRID 411525
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인쇄 미리보기

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HRID 411525 반응식
[C:1]([C:3]1[CH:29]=[CH:28][C:6]([NH:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:17][CH:16]3[CH:18]([N:19](C)[C:20](=O)[O:21]C(C)(C)C)[CH:13]([CH2:14][CH2:15]3)[CH2:12]2)=[CH:5][CH:4]=1)#[N:2].Cl>C(OCC)(=O)C>[OH-:21].[NH4+:2].[CH3:20][NH:19][CH:18]1[CH:13]2[CH2:14][CH2:15][CH:16]1[CH2:17][N:11]([CH2:10][CH2:9][CH2:8][NH:7][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:29][CH:28]=1)[CH2:12]2
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참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 18540877Tert-butyl 3-[3-(4-cyanoanilino)propyl]-3-azabicyclo[3.2.1]oct-8-yl-(methyl)carbamate

생성물 2

HCID 14923Ammonium HydroxideHCID 185408864-({3-[8-(Methylamino)-3-azabicyclo[3.2.1]oct-3-yl]propyl}amino)benzonitrile수율 107.5%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
25 °C

실험 절차

A suspension of tert-butyl 3-[3-(4-cyanoanilino)propyl]-3-azabicyclo-[3.2.1]oct-8-yl(methyl)carbamate (see step (iii) above; 2.66 g, 6.67 mmol) in ethyl acetate saturated with HCl (40 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 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 1.07 g (54%) of the title compound as a white solid.

후처리

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

출처 및 근거

ORD 기록
ord-d815d06359ed42d9a9a8b5b1ba64fd70
출처 데이터셋
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06559162B2

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