2-Chloro-N,N-dimethylethylamine → HCID 14837042, compound

HRID 2072805Notes

Reaction equation

HRID 2072805 reaction equation
C(=O)(O)[O-].[Na+].[F:6][C:7]1[C:19]([F:20])=[C:18]([F:21])[C:17]([F:22])=[C:16]([F:23])[C:8]=1[O:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27]Cl>CN(C)C=O>[CH3:24][N:25]([CH2:26][CH2:27][N:13]1[CH2:14][CH2:15][CH:10]([O:9][C:8]2[C:16]([F:23])=[C:17]([F:22])[C:18]([F:21])=[C:19]([F:20])[C:7]=2[F:6])[CH2:11][CH2:12]1)[CH3:29]

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 516892Sodium BicarbonateHCID 148370404-(2,3,4,5,6-Pentafluorophenoxy)piperidine

Product 1

HCID 14837042HCID 14837042, compoundYield 45.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
85 °C

Procedure

A stirred mixture of 5 g of sodium bicarbonate, 4.44 g of 4-(2,3,4,5,6-pentafluorophenoxy)piperidine, and 40 ml of dimethylformamide was treated, dropwise, with a solution of 2.15 g of 2-dimethylaminoethyl chloride in 20 ml of dimethylformamide. After stirring for five hours at 85° C., the reaction mixture was filtered, and the filtrate poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, evaporation of the volatiles afforded an oil which was eluted with 20% methanol/dichloromethane on a silica gel column via flash chromatography. The desired fractions were evaporated to afford 2.58 g of 1-[2-(N,N-dimethylamino)ethyl]-4-(2,3,4,5,6-pentafluorophenoxy)piperidine as an oil. The oil was dissolved in isopropanol and the solution acidified to pH 1 with etheral hydrogen chloride to precipitate 2.05 g (29.3%) of the corresponding dihydrochloride salt, m.p. 276° C. (dec.).

Workup

  1. additionwas treated
  2. filtrationthe reaction mixture was filtered
  3. additionthe filtrate poured into water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtering
  8. customevaporation of the volatiles
  9. customafforded an oil which
  10. washwas eluted with 20% methanol/dichloromethane on a silica gel column via flash chromatography
  11. customThe desired fractions were evaporated

Sources & evidence

ORD record
ord-1a9a0bb5fd634c899430b8667192b09d
Source dataset
uspto-grants-1990_04
Patent number
US04914204

Reaction notes

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