3-Chloro-N,N-dimethyl-1-propanamine → HCID 14837044, compound

HRID 1031539Notes

Reaction equation

HRID 1031539 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]([CH2:27][CH2:28][CH2:29]Cl)[CH3:26]>CN(C)C=O>[CH3:24][N:25]([CH2:27][CH2:28][CH2:29][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)[CH3:26]

Participants

5

Reactant 3

HCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 516892Sodium BicarbonateHCID 148370404-(2,3,4,5,6-Pentafluorophenoxy)piperidine

Product 1

HCID 14837044HCID 14837044, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of 10 g of sodium bicarbonate, 4.0 g of 4-(2,3,4,5,6-pentafluorophenoxy)piperidine, and 50 ml of dimethylformamide was treated, dropwise, with a solution of 2.00 g of dimethylaminopropyl chloride in 20 ml of dimethylformamide. After stirring at 80° C. for eight hours, 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 solution of sodium chloride and dried over anhydrous magnesium sulfate. After filtering, evaporation of the volatiles afforded a residue which was eluted with 20% methanol/dichloromethane on a silica gel column via flash chromatography. The desired fractions were evaporated to afford 2.74 g of 1-[3-(N,N-dimethylamino)propyl]-4-(2,3,4,5,6-pentaflurophenoxy)piperidine as an oil. The oil was dissolved in isopropanol and acidified to pH 1 with etheral hydrogen chloride to precipitate 1.8 g (28%) of 1-[3-dimethylaminopropyl]-4-(2,3,4,5,6-pentaflurophenoxy)piperidine hydrochloride, m.p. 260° 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 a residue 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-8c9d0d4c91c24dceaef177e9472f7924
Source dataset
uspto-grants-1990_09
Patent number
US04954511

Reaction notes

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