Boron trifluoride etherate → HCID 22762506, compound

HRID 1112743Notes

Reaction equation

HRID 1112743 reaction equation
[C:1]1([C:7]2[O:11][C:10]([C:12]([N:14]3[CH2:19][CH2:18][N:17]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=4)[CH2:16][CH2:15]3)=O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].B(F)(F)F.CCOCC>COCCOCCOC>[C:1]1([C:7]2[O:11][C:10]([CH2:12][N:14]3[CH2:15][CH2:16][N:17]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[CH:21]=4)[CH2:18][CH2:19]3)=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 22762602HCID 22762602, compound

Product 1

HCID 22762506HCID 22762506, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent2×

Procedure

1-(5-Phenyl-2-furoyl)-4-(3-trifluoromethylphenyl)-piperazine (6.0 g, 0.015 mole) and sodium borohydride (1.28 g, 0.034 mole) were stirred in diglyme (25 ml), under nitrogen, and redistilled boron trifluoride etherate (6 ml, 0.045 mole) in diglyme (20 ml) added dropwise with continuous stirring. The resultant clear solution was stirred at room temperature for 3 hours and then evaporated to remove diglyme. The residue was carefully diluted with water (100 ml), followed by 5NHCl (20 ml) and the mixture heated on a steam bath for 15 minutes. The mixture was cooled and made alkaline (4N NaOH) and extracted via diethyl ether. The dried ether extract (MgSO4) was evaporated to give an oil which failed to crystallise. The product was converted to the hydrochloride and then reconverted to the free base as in Example 40. The base was obtained as a mobile oil which on very strong cooling crystallised, m.p. 56° C.

Workup

  1. additionadded dropwise with continuous stirring
  2. customevaporated
  3. customto remove diglyme
  4. additionThe residue was carefully diluted with water (100 ml)
  5. temperaturethe mixture heated on a steam bath for 15 minutes
  6. temperatureThe mixture was cooled
  7. extractionextracted via diethyl ether
  8. extractionThe dried ether extract (MgSO4)
  9. customwas evaporated
  10. customto give an oil which
  11. customto crystallise
  12. customThe base was obtained as a mobile oil which
  13. temperatureon very strong cooling
  14. customcrystallised

Sources & evidence

ORD record
ord-2944e7c5b0b44d92a8fd61efcc093555
Source dataset
uspto-grants-1978_10
Patent number
US04123529

Reaction notes

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