Acetyl chloride → HCID 19762455, compound

HRID 248868Notes

Reaction equation

HRID 248868 reaction equation
Cl.[F:2][C:3]1[C:15]([F:16])=[C:14]([F:17])[C:13]([F:18])=[C:12]([F:19])[C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.C(N(CC)CC)C.[C:27](Cl)(=[O:29])[CH3:28]>ClCCl>[C:27]([N:9]1[CH2:10][CH2:11][CH:6]([O:5][C:4]2[C:12]([F:19])=[C:13]([F:18])[C:14]([F:17])=[C:15]([F:16])[C:3]=2[F:2])[CH2:7][CH2:8]1)(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 19762467HCID 19762467, compound

Product 1

HCID 19762455HCID 19762455, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirring solution of 4.76 g of 4-(2,3,4,5,6-pentafluorophenoxy)piperidine hydrochloride in 100 ml of dichloromethane was treated with 4.46 ml of triethyl amine followed by a solution of 1.413 g of acetyl chloride in 60 ml of dichloromethane (dropwise). After stirring at ambient temperature for 18 hours, the reaction mixture was washed with water followed by a saturated solution of sodium chloride and dried over anhydrous magnesium sulfate. Filtration, followed by evaporation of the solvents afforded an oil which was purified by means of high pressure liquid chromatography (silica gel; elution with 10% ethyl acetate/dichloromethane). The resultant oil solidified upon standing and this material was sublimed to 3.2 g (64.7%) of 1-acetyl-4-(2,3,4,5,6-pentafluorophenoxy)piperidine, m.p. 60°-65° C.

Workup

  1. washthe reaction mixture was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationFiltration
  4. customfollowed by evaporation of the solvents
  5. customafforded an oil which
  6. customwas purified by means of high pressure liquid chromatography (silica gel; elution with 10% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-2f5128bb5fb24ce8bbdb2da8da5b1648
Source dataset
uspto-grants-1993_05
Patent number
US05212184

Reaction notes

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