Palmitoyl chloride → 4-(4-Palmitoylamino-2-methylphenyloxy)piperidine hydrochloride

HRID 1079403Notes

Reaction equation

HRID 1079403 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:16]=2[CH3:22])[CH2:10][CH2:9]1)=O)(C)(C)C.C(N(CC)CC)C.[C:30]([Cl:47])(=[O:46])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[ClH:47].[C:30]([NH:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[C:16]([CH3:22])[CH:17]=1)(=[O:46])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]

Participants

6

Reactant 4

HCID 8206Palmitoyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 22181171Tert-butyl 4-(4-amino-2-methylphenoxy)piperidine-1-carboxylate

Product 1

HCID 233669014-(4-Palmitoylamino-2-methylphenyloxy)piperidine hydrochlorideYield 85.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-tert-butyloxycarbonyl-4-(4-amino-2-methylphenyloxy)piperidine (1.5 g) in methylene chloride (30 ml) were added triethylamine (1.3 g) and palmitoyl chloride (1.2 g) with ice-cooling and the mixture was stirred at room temperature for 1 hour. Aqueous saturated solution of sodium bicarbonate was added to the reaction mixture and the organic layer was separated. The aqueous layer was further extracted with methyene chloride (50 ml×2) and the combined orgnaic layer was dried over sodium sulfate and concentrated under reduced pressure. To the solidified residue was added trifluoroacetic acid (5 ml) and the mixture was stirred at room temperature for 30 minutes. After concentration of the reaction mixture under reduced pressure, the resulting residue was dissolved in ethanol and conc. hydrochloric acid (0.37 ml) was added. The resulting solution was concentrated under reduced pressure and the residue was washed with hexane to obtain 4-(4-palmitoylamino-2-methylphenyloxy)piperidine hydrochloride (1.8 g) as white crystals, m.p. 125°-137° C.

Workup

  1. temperaturecooling
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was further extracted with methyene chloride (50 ml×2)
  4. dry with materialthe combined orgnaic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo the solidified residue was added trifluoroacetic acid (5 ml)
  7. stirringthe mixture was stirred at room temperature for 30 minutes
  8. dissolutionAfter concentration of the reaction mixture under reduced pressure, the resulting residue was dissolved in ethanol
  9. additionconc. hydrochloric acid (0.37 ml) was added
  10. concentrationThe resulting solution was concentrated under reduced pressure
  11. washthe residue was washed with hexane

Sources & evidence

ORD record
ord-a6c1d879d99245e6a3205cbf33d63e4f
Source dataset
uspto-grants-1996_12
Patent number
US05580883

Reaction notes

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