2,2,2-Trifluoroethylamine hydrochloride → HCID 61392703, compound

HRID 1771423Notes

Reaction equation

HRID 1771423 reaction equation
Cl.[F:2][C:3]([F:7])([F:6])[CH2:4]N.N([O-])=O.[Na+].[C:12]1([CH3:21])[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][CH:19]=[O:20].C([O-])(O)=O.[Na+]>ClCCl.O.[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4].CO>[F:2][C:3]([F:7])([F:6])[CH2:4][CH:19]([OH:20])[CH2:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH3:21]

Participants

8

Reactant 4

HCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 66286Benzeneacetaldehyde, 2-methyl-HCID 516892Sodium BicarbonateHCID 23668193Sodium Nitrite

Product 1

HCID 61392703HCID 61392703, compound

Reagents, catalysts & solvents 3

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-CatalystHCID 887MethanolSolventHCID 21908982Water methylene chlorideSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 2,2,2-trifluoroethylamine hydrochloride (0.271 g) in dichloromethane/water (15/0.5 mL) at 0° C. was added sodium nitrite (0.166 g) and the resulting yellow solution was stirred for 1 hour at 0° C. The reaction mixture was then cooled to −78° C. and 2-o-tolylacetaldehyde (0.134 g) was added, followed by zirconium(IV)tetrachloride. After stirring for 2 hrs at −78° C. cooling was stopped and methanol (3 mL) and saturated solution of NaHCO3 (10 mL) were added. The mixture was extracted with dichloromethane and the extracts were dried and concentrated. Evaporation residue (194 mg) was dissolved in methanol (3 ml) and solution was cooled to 0° C. Sodium borohydride (44 mg) was added and the reaction mixture was stirred for 25 minutes. K2CO3-solution (2M, 5 mL) was added to the reaction mixture, followed by water (5 mL) after 5 min and the resulting solution was extracted with EtOAc. Extracts were dried and concentrated and the residue was purified by separation method E (EtOAc/heptane). (Yield 121 mg).

Workup

  1. temperatureThe reaction mixture was then cooled to −78° C.
  2. stirringAfter stirring for 2 hrs at −78° C.
  3. temperaturecooling
  4. extractionThe mixture was extracted with dichloromethane
  5. customthe extracts were dried
  6. concentrationconcentrated
  7. customEvaporation residue (194 mg)
  8. dissolutionwas dissolved in methanol (3 ml)
  9. temperaturesolution was cooled to 0° C
  10. additionSodium borohydride (44 mg) was added
  11. stirringthe reaction mixture was stirred for 25 minutes
  12. additionK2CO3-solution (2M, 5 mL) was added to the reaction mixture
  13. waitfollowed by water (5 mL) after 5 min
  14. extractionthe resulting solution was extracted with EtOAc
  15. customExtracts were dried
  16. concentrationconcentrated
  17. customthe residue was purified by separation method E (EtOAc/heptane)

Sources & evidence

ORD record
ord-827c2d440e5c4f86bca3c58295c6b068
Source dataset
uspto-grants-2016_02
Patent number
US09249127B2

Reaction notes

Loading…