4-Heptanone → HCID 68471227, compound

HRID 387663Notes

Reaction equation

HRID 387663 reaction equation
Cl.[Br:2][C:3]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:4]=1[CH2:5][CH2:6][NH2:7].[CH3:16][CH2:17][CH2:18][C:19](=O)[CH2:20][CH2:21][CH3:22].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClC(Cl)C.O.C(N(CC)CC)C>[Br:2][C:3]1[CH:11]=[C:10]([C:12]([F:13])([F:14])[F:15])[CH:9]=[CH:8][C:4]=1[CH2:5][CH2:6][NH:7][CH:19]([CH2:20][CH2:21][CH3:22])[CH2:18][CH2:17][CH3:16]

Participants

8

Reactant 4

HCID 312464-HeptanoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 131730208HCID 131730208, compound

Product 1

HCID 68471227HCID 68471227, compoundYield 96.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolventHCID 8471TriethylamineSolvent

Procedure

Added to a suspension of 1 g of 2-bromo-4-trifluoromethylphenethylamine hydrocloride in 25 cm3 of dichloroethane and under an inert atmosphere is 0.5 cm3 of triethylamine. After stirring for 30 min at a temperature close to 20° C., 5 cm3 of distilled water are added and the stirring is continued for 30 min. The two phases are separated and the organic phase is dried. Added to the solution obtained are successively 375 mg of 4-heptanone and 970 mg of sodium triacetoxyborohydride. The reaction mixture is stirred for 15 h at a temperature close to 20° C. 20 cm3 of a saturated solution of sodium hydrogen carbonate are then added to the reaction medium. The organic phase is decanted and separated from the aqueous phase then washed successively with 15 cm3 of distilled water and 15 cm3 of a saturated solution of sodium chloride. The organic phase is dried then concentrated using a rotary evaporator under reduced pressure (5 kPa). 1.16 g of N-[2-(2-bromo-4-trifluoromethylphenyl)ethyl]heptan-4-amine are obtained in the form of a colorless oil.

Workup

  1. customclose to 20° C.
  2. waitthe stirring is continued for 30 min
  3. customThe two phases are separated
  4. customthe organic phase is dried
  5. additionAdded to the solution
  6. customobtained
  7. stirringThe reaction mixture is stirred for 15 h at a temperature
  8. customclose to 20° C
  9. customThe organic phase is decanted
  10. customseparated from the aqueous phase
  11. washthen washed successively with 15 cm3 of distilled water and 15 cm3 of a saturated solution of sodium chloride
  12. customThe organic phase is dried
  13. concentrationthen concentrated
  14. customa rotary evaporator under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-e628a63ecdb64a70bdec3918cb9c8c45
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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