Benzoyl Peroxide → HCID 53945497, compound

HRID 1684755Notes

Reaction equation

HRID 1684755 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH3:17].Br[N:20]1[C:24](=O)[CH2:23][CH2:22][C:21]1=O.C(OOC(=O)C1C=CC=CC=1)(=[O:34])C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:20]2[CH2:24][CH2:23][O:34][CH2:22][CH2:21]2)=[CH:6][C:5]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH3:17]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 53730226HCID 53730226, compound

Product 1

HCID 53945497HCID 53945497, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

The 2-(4-methoxybutoxy)-4-(morpholin-4-ylmethyl)-benzoic acid methyl ester that is used is prepared as follows: A mixture of 2-(4-methoxybutoxy)-4-methyl-benzoic acid methyl ester (1.0 g), N-bromosuccinimide (0.70 g), 2',2"-azoisobutyronitrile (23 mg) and dibenzoyl peroxide (34 mg) in carbon tetrachloride (10 ml) is stirred under reflux for 5 hours. After cooling to room temperature, the precipitate is filtered off, morpholine (1.03 ml) is added to the filtrate, and stirring is carried out for a further 2 hours at room temperature. The crude product obtained after filtration and concentration is purified by FC on silica gel (40 g, eluant gradient from C to F). The title compound, Rf (F)=0.14, is obtained in the form of a yellowish oil.

Workup

  1. temperatureunder reflux for 5 hours
  2. filtrationthe precipitate is filtered off
  3. additionmorpholine (1.03 ml) is added to the filtrate
  4. stirringstirring
  5. customThe crude product obtained

Sources & evidence

ORD record
ord-f5d8a8d8bfc34bfaad7496d032778b2b
Source dataset
uspto-grants-1997_06
Patent number
US05641778

Reaction notes

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