1-Phenyl-1,3,8-triazaspiro(4.5)decan-4-one → HCID 21428981, compound

HRID 437628Notes

Reaction equation

HRID 437628 reaction equation
[Br:1][CH2:2][CH2:3][NH:4][C:5](=[O:15])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13].[C:16]1([N:22]2[C:26]3([CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[C:25](=[O:32])[NH:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O>[BrH:1].[N+:12]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:5]([NH:4][CH2:3][CH2:2][N:29]1[CH2:28][CH2:27][C:26]2([N:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:23][NH:24][C:25]2=[O:32])[CH2:31][CH2:30]1)=[O:15])([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 3017373N-(2-Bromoethyl)-2-nitrobenzene-1-carboximidic acid

Product 1

HCID 21428981HCID 21428981, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.2 parts of N-(2-bromoethyl)-2-nitrobenzamide, 1.15 parts of 1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one and 45 parts of N,N-dimethylformamide is stirred and refluxed for 3 hours. After stirring is continued overnight at room temperature, N,N-dimethylformamide is evaporated in vacuo at 80° C. The residue is boiled in a mixture of 2-propanone and water and the unreacted starting material is filtered off. The filtrate is concentrated to half its volume and 2-propanol is added to the concentrate. The precipitated product is filtered off and dried, yielding 7 parts of 2-nitro-N-[2-(4-oxo-1-phenyl-1,3,8-triazaspiro[4,5]dec-8-yl)-ethyl]benzamide hydrobromide; mp. 259.4° C.

Workup

  1. temperaturerefluxed for 3 hours
  2. stirringAfter stirring
  3. customN,N-dimethylformamide is evaporated in vacuo at 80° C
  4. additionThe residue is boiled in a mixture of 2-propanone and water
  5. filtrationis filtered off
  6. concentrationThe filtrate is concentrated to half its volume and 2-propanol
  7. additionis added to the concentrate
  8. filtrationThe precipitated product is filtered off
  9. customdried

Sources & evidence

ORD record
ord-c3d87556b60d4b658aaf47bcb0f32d8c
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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