Dimethylcarbamoyl Chloride → HCID 19762459, compound

HRID 248864Notes

Reaction equation

HRID 248864 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[F:8][C:9]1[C:21]([F:22])=[C:20]([F:23])[C:19]([F:24])=[C:18]([F:25])[C:10]=1[O:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[CH3:26][N:27]([CH3:31])[C:28](Cl)=[O:29]>O.C(Cl)(Cl)Cl>[CH3:26][N:27]([C:28]([N:15]1[CH2:16][CH2:17][CH:12]([O:11][C:10]2[C:18]([F:25])=[C:19]([F:24])[C:20]([F:23])=[C:21]([F:22])[C:9]=2[F:8])[CH2:13][CH2:14]1)=[O:29])[CH3:31]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 19762467HCID 19762467, compound

Product 1

HCID 19762459HCID 19762459, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

To a stirring solution of 10 g of potassium carbonate in 50 ml of water was added 4.42 g of 4-(2,3,4,5,6-pentafluorophenoxy)piperidine hydrochloride in 50 ml of chloroform, followed by a solution of 3.23 g of dimethylcarbamoyl chloride in 20 ml of chloroform which was added, dropwise, over a period of 20 minutes. After stirring for 20 hours at room temperature, the layers were separated; the organic layer was washed with water followed by a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. Filtration, followed by evaporation of the filtrate afforded an oil. The oil was purified by means of high pressure liquid chromatography (silica gel; elution with 5% methanol/dichloromethane) to afford 3.50 g (69.0%) of 1-[(N,N-dimethylamino)carbonyl]-4-(2,3,4,5,6-pentafluorophenoxy)piperidine as an oil.

Workup

  1. additionwas added
  2. customthe layers were separated
  3. washthe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationFiltration
  6. customfollowed by evaporation of the filtrate
  7. customafforded an oil
  8. customThe oil was purified by means of high pressure liquid chromatography (silica gel; elution with 5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-9c2c0f3f4a084acea51e7367068aceed
Source dataset
uspto-grants-1993_05
Patent number
US05212184

Reaction notes

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