4-Heptanone → HCID 68473149, compound

HRID 387686Notes

Reaction equation

HRID 387686 reaction equation
Cl.[Br:2][C:3]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:4]=1[CH2:5][CH2:6][NH2:7].[CH3:13][CH2:14][CH2:15][C:16](=O)[CH2:17][CH2:18][CH3:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCl.O.C(N(CC)CC)C>[Br:2][C:3]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:4]=1[CH2:5][CH2:6][NH:7][CH:16]([CH2:17][CH2:18][CH3:19])[CH2:15][CH2:14][CH3:13]

Participants

8

Reactant 4

HCID 312464-HeptanoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 131730210HCID 131730210, compound

Product 1

HCID 68473149HCID 68473149, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Added to a suspension of 1 g of 2-bromo-4-fluorophenethylamine hydrocloride in 25 cm3 of dichloromethane and under an inert atmosphere is 663 μL 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. 15 cm3 of distilled water are added and the two phases are separated. The organic phase is washed with three lots of 10 cm3 of distilled water, then dried. Added to the solution obtained are successively 449 mg of 4-heptanone and 1.166 g 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). 1.069 g of N-[2-(2-bromo-4-fluorophenyl)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. washThe organic phase is washed with three lots of 10 cm3 of distilled water
  5. customdried
  6. additionAdded to the solution
  7. customobtained
  8. stirringThe reaction mixture is stirred for 15 h at a temperature
  9. customclose to 20° C
  10. customThe organic phase is decanted
  11. customseparated from the aqueous phase
  12. washthen washed successively with 15 cm3 of distilled water and 15 cm3 of a saturated solution of sodium chloride
  13. customThe organic phase is dried
  14. concentrationthen concentrated
  15. customa rotary evaporator under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-2abb232722324d7aa6561937577aba3d
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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