4-Cyanobenzoyl chloride → 9-(4-Cyanobenzoyl)-3-oxo-1-oxa-4,9-diaza-spiro[5.5]undecane

HRID 2120958Notes

Reaction equation

HRID 2120958 reaction equation
Br.[O:2]=[C:3]1[NH:8][CH2:7][C:6]2([CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[O:5][CH2:4]1.[C:14]([C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1)#[N:15]>N1C=CC=CC=1>[C:14]([C:16]1[CH:24]=[CH:23][C:19]([C:20]([N:11]2[CH2:12][CH2:13][C:6]3([O:5][CH2:4][C:3](=[O:2])[NH:8][CH2:7]3)[CH2:9][CH2:10]2)=[O:21])=[CH:18][CH:17]=1)#[N:15]

Participants

4

Reactant 2

HCID 801724-Cyanobenzoyl chlorideHCID 23435708HCID 23435708, compound

Product 1

HCID 234357029-(4-Cyanobenzoyl)-3-oxo-1-oxa-4,9-diaza-spiro[5.5]undecane

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

18.0 g (71.7 mmol) 3-oxo-1-oxa-4,9-diaza-spiro[5.5]undecane hydrobromide (prepared according to J. Med. Chem. 1983, 26, 855) were dissolved in 300 ml dry pyridine, and 11.9 g (71.9 mmol) 4-cyanobenzoyl chloride were added in small portions. The mixture was stirred over night at room temperature and evaporated under reduced pressure. The residue was dissolved in toluene, which was removed in vacuo. This process was repeated two times to remove remaining pyridine. It was treated with water and neutralized by addition of saturated aqueous sodium bicarbonate solution. The precipitate of the title compound was filtered with suction, washed with water, and dried in vacuo.

Workup

  1. customevaporated under reduced pressure
  2. dissolutionThe residue was dissolved in toluene
  3. customwhich was removed in vacuo
  4. customto remove
  5. additionIt was treated with water
  6. additionneutralized by addition of saturated aqueous sodium bicarbonate solution
  7. filtrationThe precipitate of the title compound was filtered with suction
  8. washwashed with water
  9. customdried in vacuo

Sources & evidence

ORD record
ord-44f848d1bbeb4094917fb72d7b46314d
Source dataset
uspto-grants-2004_02
Patent number
US06693109B2

Reaction notes

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