Triethylamine → 4-(4-Decanoylamino-3-methylphenyloxy)piperidine hydrochloride

HRID 1079405Notes

Reaction equation

HRID 1079405 reaction equation
Cl.C(OC([N:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([CH3:23])[CH:17]=2)[CH2:11][CH2:10]1)=O)(C)(C)C.C(N(CC)CC)C.[C:31]([Cl:42])(=[O:41])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40].C(OC([O-])=O)([O-])=O.[Na+].[Na+]>C(Cl)Cl>[ClH:42].[C:31]([NH:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][CH:12]2[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]2)=[CH:17][C:18]=1[CH3:23])(=[O:41])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 66982Decanoyl chlorideHCID 22718997Sodium dicarbonateHCID 233668921-Tert-butyloxycarbonyl-4-(4-amino-3-methylphenyloxy)piperidine hydrochloride

Product 1

HCID 233669194-(4-Decanoylamino-3-methylphenyloxy)piperidine hydrochlorideYield 114.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-tert-butyloxycarbonyl-4-(4-amino-3-methylphenyloxy)piperidine hydrochloride (0.7 g) in methylene chloride (10 ml) were added triethylamine (0.62 g) and decanoyl chloride (0.39 g) with ice-cooling and the mixture was stirred at room temperature for 1 hour. Aqueous saturated solution of sodium dicarbonate was added to the reaction mixture and the organic layer was separated. The aqueous layer was further extracted with methylene chloride (50 ml×2) and the combined organic 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. The reaction mixture was concentrated under reduced pressure, the resulting residue was dissolved in ethanol and conc. hydrochloric acid (0.20 ml) was added thereto. The resulting solution was concentrated under reduced pressure and the residue was washed with hexane to obtain 4-(4-decanoylamino-3-methylphenyloxy)piperidine hydrochloride (0.93 g) as white crystals, m.p. 177°-195° C.

Workup

  1. temperaturecooling
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was further extracted with methylene chloride (50 ml×2)
  4. dry with materialthe combined organic 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. concentrationThe reaction mixture was concentrated under reduced pressure
  9. dissolutionthe resulting residue was dissolved in ethanol
  10. additionconc. hydrochloric acid (0.20 ml) was added
  11. concentrationThe resulting solution was concentrated under reduced pressure
  12. washthe residue was washed with hexane

Sources & evidence

ORD record
ord-695985e6a9534c38b12238f71f1209c8
Source dataset
uspto-grants-1996_12
Patent number
US05580883

Reaction notes

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