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Hydrochloric Acid → 2-[4-[(Dimethylamino)methyl]phenyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one

HRID 448767
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HRID 448767 반응식
[OH-].[Na+].C[O:4][C:5]([C:7]1([NH:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][N:23]([CH3:25])[CH3:24])=[CH:18][CH:17]=2)=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=O.Cl.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>O1CCCC1.C(Cl)Cl>[CH3:24][N:23]([CH2:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]2[O:15][C:5](=[O:4])[C:7]3([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]3)[N:13]=2)=[CH:17][CH:18]=1)[CH3:25]
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참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 576728621-[[[4-[(Dimethylamino)methyl]phenyl]carbonyl]amino]cyclohexanecarboxylic acid methyl ester

생성물 1

HCID 57672908
2-[4-[(Dimethylamino)methyl]phenyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one
수율 80.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

29 ml of 2N aqueous sodium hydroxide solution was added to a solution of 1.85 g (5.8 mmol) of 1-[[[4-[(dimethylamino)methyl]phenyl]carbonyl]amino]cyclohexanecarboxylic acid methyl ester in 29 ml of tetrahydrofuran, and the mixture was heated under reflux overnight. After the mixture was neutralized by concentrated hydrochloric acid, the reaction solution was distilled off under reduced pressure. 30 ml of methylene chloride, 1.76 g (17 mmol) of triethylamine and 1.67 g (8.7 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were added to the residue, and the mixture was stirred for 1 hour. The reaction solution was distilled off under reduced pressure, a saturated aqueous sodium bicarbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium bicarbonate solution, and it was dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 1.33 g (80%) of the title compound.

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. distillationthe reaction solution was distilled off under reduced pressure
  4. distillationThe reaction solution was distilled off under reduced pressure
  5. additiona saturated aqueous sodium bicarbonate solution was added
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution, and it
  8. dry with materialwas dried with anhydrous sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-42c8b2716c0149fba6ae00611d0cf117
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08481725B2

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