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

HRID 410151Notes

Reaction equation

HRID 410151 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5288017f10b44edc80faab37aab01b6e
Source dataset
uspto-grants-2014_06
Patent number
US08759586B2

Reaction notes

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