Hydrochloric Acid → N-[(2,4-difluorophenyl)methyl]-N-hexyl-2,2-dimethylpentanamide

HRID 974402Notes

Reaction equation

HRID 974402 reaction equation
[CH2:1]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[F:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(N(CC)CC)C.[CH3:24][C:25]([CH3:32])([CH2:29][CH2:30][CH3:31])[C:26](Cl)=[O:27].Cl>C(OCC)C>[F:16][C:10]1[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=1[CH2:8][N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:26](=[O:27])[C:25]([CH3:32])([CH3:24])[CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 5191712,2-Dimethylvaleroyl chlorideHCID 19986431N-Hexyl-2,4-difluorobenzylamine

Product 1

HCID 19986408N-[(2,4-difluorophenyl)methyl]-N-hexyl-2,2-dimethylpentanamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

22.7 g (0.10 mol) of N-hexyl-2,4-difluorobenzylamine and 24.3 g (0.24 mol) of triethylamine are dissolved in 150 ml of diethyl ether. A solution of 17.8 g (0.12 mol) of 2,2-dimethylpentanoyl chloride in 50 ml of diethyl ether is added dropwise at room temperature over the course of 30 minutes. The mixture is stirred for a further 18 hours at room temperature until the reaction is complete (GC check). For work-up, the resultant suspension is adjusted to pH 7 using 70 ml of 2N hydrochloric acid. Everything dissolves, and two phases form, which are separated. The organic phase is washed with 50 ml of water, dried using magnesium sulfate, filtered and evaporated on a vacuum rotary evaporator. 37.8 g of a pale yellow liquid, which is subjected to fractional distillation, are obtained. 21.4 g (63% of theory) of a colourless oil which boils at 126°-127° C. and 0.4 mbar are obtained.

Workup

  1. dissolutionEverything dissolves
  2. customtwo phases form, which are separated
  3. washThe organic phase is washed with 50 ml of water
  4. customdried
  5. filtrationfiltered
  6. customevaporated on a vacuum rotary evaporator
  7. distillation37.8 g of a pale yellow liquid, which is subjected to fractional distillation
  8. customare obtained
  9. custom21.4 g (63% of theory) of a colourless oil which boils at 126°-127° C. and 0.4 mbar are obtained

Sources & evidence

ORD record
ord-fe2b8316ba6441fdaffddef32041f8b6
Source dataset
uspto-grants-1991_11
Patent number
US05068371

Reaction notes

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