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

HRID 411525
ノート
印刷プレビュー

反応式

HRID 411525 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d815d06359ed42d9a9a8b5b1ba64fd70
出典データセット
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06559162B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート