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

HRID 1851841Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1851841
[OH-].[Na+].C1(C[O:10][C:11]([C:13]2([NH:19][C:20]([C:22]3[CH:27]=[CH:26][C:25]([CH2:28][N:29]([CH3:31])[CH3:30])=[CH:24][CH:23]=3)=O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])C=CC=CC=1.Cl.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>O1CCCC1.C(Cl)Cl>[CH3:30][N:29]([CH2:28][C:25]1[CH:26]=[CH:27][C:22]([C:20]2[O:10][C:11](=[O:12])[C:13]3([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]3)[N:19]=2)=[CH:23][CH:24]=1)[CH3:31]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 576728851-[[[4-[(Dimethylamino)methyl]phenyl]carbonyl]amino]cyclohexanecarboxylic acid phenylmethyl ester

Produkt 1

HCID 576729082-[4-[(Dimethylamino)methyl]phenyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-oneAusbeute 72,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

0.7 ml of 2N aqueous sodium hydroxide solution was added to a solution of 100 mg (0.25 mmol) of 1-[[[4-[(dimethylamino)methyl]phenyl]carbonyl]amino]cyclohexanecarboxylic acid phenylmethyl ester in 1 ml of tetrahydrofuran, and the mixture was refluxed under heating overnight. After the mixture was neutralized by concentrated hydrochloric acid, the reaction mixture was distilled off under reduced pressure. 3 ml of methylene chloride, 126 mg (1.25 mmol) of triethylamine and 96 mg (0.5 mmol) 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were added to the residue, the mixture was stirred for 1 hour. The reaction mixture was distilled off under reduced pressure, an 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 dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 52 mg (68%) of the title compound.

Aufarbeitung

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating overnight
  3. distillationthe reaction mixture was distilled off under reduced pressure
  4. distillationThe reaction mixture was distilled off under reduced pressure
  5. additionan 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
  8. dry with materialdried with anhydrous sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a60ef2fb13534d5aa3dd50fc75d9bc9f
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957205B2

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