Ethyl Acetate → N-[(1R)-1-(naphthalen-1-yl)ethyl]-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-amine fumarate

HRID 410151

反応式

HRID 410151 の反応式
[C:1](=[O:4])([OH:3])[O-].[Na+].Cl.[C:7]1([C@H:17]([NH:19][CH2:20][CH:21]=[CH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)[CH3:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1.[C:33]([O:36]CC)(=[O:35])[CH3:34]>>[C:33]([OH:36])(=[O:35])/[CH:34]=[CH:7]/[C:1]([OH:3])=[O:4].[C:7]1([C@H:17]([NH:19][CH2:20][CH:21]=[CH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:31])[F:32])[CH:24]=2)[CH3:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1

参加物

4

反応物 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 67057068N-[(1R)-1-(naphthalen-1-yl)ethyl]-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-amine hydrochloride

生成物 1

HCID 67057018N-[(1R)-1-(naphthalen-1-yl)ethyl]-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-amine fumarate

実験手順

Aqueous solution of sodium bicarbonate (5% in water; 30 mL) was added to a solution of N-[(1R)-1-(naphthalen-1-yl)ethyl]-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-amine hydrochloride (5.0 g) in ethyl acetate (30 mL) at room temperature and stirred for 1 hour. After completion of the reaction, product was extracted with ethyl acetate (50 mL). The organic layer was washed with water (30 mL), passed through hyflo bed and hyflo bed was washed with ethyl acetate (10 mL). The ethyl acetate layer was concentrated to about 30 mL. Fumaric acid (2 g) was added to the concentrated ethyl acetate layer at room temperature and stirred for about one hour to obtain the precipitates of N-[(1R)-1-(naphthalen-1-yl)ethyl]-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-amine fumarate. The solid was filtered, washed with ethyl acetate twice (2×10 mL) and dried under vacuum.

後処理

  1. customAfter completion of the reaction, product
  2. extractionwas extracted with ethyl acetate (50 mL)
  3. washThe organic layer was washed with water (30 mL)
  4. washwas washed with ethyl acetate (10 mL)
  5. concentrationThe ethyl acetate layer was concentrated to about 30 mL
  6. additionFumaric acid (2 g) was added to the concentrated ethyl acetate layer at room temperature
  7. stirringstirred for about one hour
  8. customto obtain the
  9. customprecipitates of N-[(1R)-1-(naphthalen-1-yl)ethyl]-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-amine fumarate
  10. filtrationThe solid was filtered
  11. washwashed with ethyl acetate twice (2×10 mL)
  12. customdried under vacuum

出典と根拠

ORDレコード
ord-5288017f10b44edc80faab37aab01b6e
出典データセット
uspto-grants-2014_06
特許番号
US08759586B2

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