Water → Ethyl (3-oxo-1-phenyl-1,4-diazaspiro[5.5]undec-4-yl)acetate

HRID 1894861Notes

Reaction equation

HRID 1894861 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1([NH:13][C:14]2([CH2:20][NH:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl[CH2:29][C:30](Cl)=[O:31].O>CN(C)C=O>[O:31]=[C:30]1[N:21]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:20][C:14]2([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[N:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:29]1

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 86646976Ethyl [(1-phenylaminocyclohexylmethyl)amino]acetate

Product 1

HCID 86646979Ethyl (3-oxo-1-phenyl-1,4-diazaspiro[5.5]undec-4-yl)acetateYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

95 mg (0.69 mmol) of potassium carbonate are added to a solution of 200 mg (0.69 mmol) of ethyl [(1-phenylaminocyclohexylmethyl)amino]-acetate and 55 μl (0.69 mmol) of chloroacetyl chloride in 15 ml of dimethylformamide. The reaction medium is stirred at reflux for 6 h and poured into water and extracted with ethyl acetate. The organic phases are collected and washed with water. They are dried over sodium sulfate. The solvents are evaporated. 220 mg of ethyl (3-oxo-1-phenyl-1,4-diazaspiro[5.5]undec-4-yl)acetate are obtained in the form of an orange oil. Yield=97%.

Workup

  1. temperatureat reflux for 6 h
  2. extractionextracted with ethyl acetate
  3. customThe organic phases are collected
  4. washwashed with water
  5. dry with materialThey are dried over sodium sulfate
  6. customThe solvents are evaporated

Sources & evidence

ORD record
ord-4f23c8d1401142da94dce7892fd7b8ba
Source dataset
uspto-grants-2013_08
Patent number
US08513307B2

Reaction notes

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