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

HRID 1079405노트

반응식

HRID 1079405 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-695985e6a9534c38b12238f71f1209c8
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05580883

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