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

HRID 1627479Notes

Reaction equation

HRID 1627479 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6].Cl.C([N:16](CC)CC)C.Cl.C(N=C=N[CH2:27][CH2:28][CH2:29][N:30]([CH3:32])[CH3:31])C.O1[CH2:37][CH2:36][CH2:35][CH2:34]1>C(Cl)Cl>[CH3:32][N:30]([CH2:29][C:28]1[CH:27]=[CH:37][C:36]([C:3]2[O:4][C:5](=[O:6])[C:7]3([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]3)[N:16]=2)=[CH:35][CH:34]=1)[CH3:31]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 20748Methyl cyclohexanecarboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 576729082-[4-[(Dimethylamino)methyl]phenyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 reaction 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 dried with anhydrous sodium sulfate.

Workup

  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
  8. dry with materialdried with anhydrous sodium sulfate

Sources & evidence

ORD record
ord-cfd7c6d28c41490b80f6c7a82ed548fc
Source dataset
uspto-grants-2014_07
Patent number
US08785631B2

Reaction notes

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