Hydrochloric Acid → 4-Chloro-2-[[(1R)-4-[ethyl(2-hydroxyethyl)amino]-1-phenylbutyl]oxy]-benzonitrile hydrochloride

HRID 352107ノート

反応式

HRID 352107 の反応式
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C@@H:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:13][CH2:14]I)[CH:3]=1.[CH2:22]([NH:24][CH2:25][CH2:26][OH:27])[CH3:23].Cl>O1CCCC1.C(OCC)C.ClCCl.C(OCC)C>[ClH:1].[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C@@H:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:13][CH2:14][N:24]([CH2:22][CH3:23])[CH2:25][CH2:26][OH:27])[CH:3]=1

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 80722-(Ethylamino)ethanolHCID 698282664-Chloro-2-[[(1r)-4-iodo-1-phenylbutyl]oxy]benzonitrile

生成物 1

HCID 698289354-Chloro-2-[[(1R)-4-[ethyl(2-hydroxyethyl)amino]-1-phenylbutyl]oxy]-benzonitrile hydrochloride収率 65.4%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒HCID 21881112Ethyl ether methylene chloride溶媒

実験手順

A solution of the product from Example 1 step (c) (200 mg) and 2-(ethylamino)ethanol (163 mg, 0.14 ml) in tetrahydrofuran (5 ml) was stirred for 2 days. The solvent was removed in vacuo and the residue dissolved in water and aqueous potassium carbonate and extracted with ethyl acetate (three times). The combined organic extracts were washed with water, dried (Na2SO4) and evaporated to give an oil. To a solution of this amine in diethyl ether-dichloromethane was added a 1M solution of hydrogen chloride in diethyl ether. The crystals that formed were collected and dried to afford the title compound as a white solid (65 mg). M.p. 141-144° C.

後処理

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in water
  3. extractionaqueous potassium carbonate and extracted with ethyl acetate (three times)
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customto give an oil
  8. customThe crystals that formed
  9. customwere collected
  10. customdried

出典と根拠

ORDレコード
ord-1479a23a332f49c69d0922977bfafd6d
出典データセット
uspto-grants-2004_06
特許番号
US06743939B2

反応ノート

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