Benzoyl Peroxide → HCID 21910590, compound

HRID 1245291Notes

Reaction equation

HRID 1245291 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10](=[O:21])[N:11]([CH3:20])[C:12]3([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[C:13]=2[CH3:14])=[CH:5][CH:4]=1.[Br:22]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Br:22][CH2:14][C:13]1[C:12]2([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[N:11]([CH3:20])[C:10](=[O:21])[C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 21910659HCID 21910659, compound

Product 1

HCID 21910590HCID 21910590, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

3-(4-Methoxyphenyl)-1,4-dimethyl-1-azaspiro[4.5]dec-3-ene-2-one (881 mg, 3.09 mmol) and N-bromosuccinimide (1.2 eq.) were stirred in 40 mL CCl4 with a catalytic amount of benzoyl peroxide for 3 h at 85° C. After cooling to room temperature the mixture was diluted with CH2Cl2, washed with water, dried (Na2SO4) and evaporated. The 4-bromomethyl-3-(4-methoxyphenyl)-1-methyl-1-azaspiro[4.5]dec-3-ene-2-one thus obtained was dissolved in ethanol (100 mL), CH2Cl2 (20 mL), and ethylamine (70% solution in water, 2 mL), the mixture was stirred overnight at room temperature and concentrated. The residue was dissolved in CH2Cl2, washed with water and extracted with 0.5 M HCl.

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-eb949f7817154f32a73c37943d1cae7b
Source dataset
uspto-grants-2006_10
Patent number
US07125840B2

Reaction notes

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