Acetyl chloride → HCID 20150309, compound
Reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:10]=[C:9]2[O:22][CH2:23][C:24]([N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)=[O:25].C(N(CC)CC)C>C(Cl)Cl>[C:1]([NH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH:10]=[C:9]2[O:22][CH2:23][C:24]([N:26]1[CH2:27][CH2:28][O:29][CH2:30][CH2:31]1)=[O:25])(=[O:3])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
A solution of acetyl chloride (0.55 cc) in methylene chloride (5 cc) is added in the course of 10 minutes to a stirred solution of 4-[(6-amino-2-phenyl-4-quinolyl)oxyacetyl]morpholine (2.55 g), prepared according to Example 39, and triethylamine (1.2 cc) in methylene chloride (25 cc). The mixture is stirred for 1 hour at room temperature (approximately 20° C.) and the solvent evaporated off under reduced pressure. The residue is stirred for 10 minutes in an ethyl acetate/water (5:2 by volume) mixture, filtered off, dissolved in a toluene/acetic acid (50:50 by volume) mixture and precipitated with ethyl ether. After filtration and drying, 4-[(6-acetylamino-2-phenyl-4-quinolyl)oxyacetyl]morpholine (2 g), m.p. 261° C., is isolated.
Workup
- customprepared
- customthe solvent evaporated off under reduced pressure
- stirringThe residue is stirred for 10 minutes in an ethyl acetate/water (5:2 by volume) mixture
- filtrationfiltered off
- dissolutiondissolved in a toluene/acetic acid (50:50 by volume) mixture
- customprecipitated with ethyl ether
- filtrationAfter filtration
- customdrying
Sources & evidence
- ORD record
- ord-6c886343ac3349fc911266c05cadb8dc
- Source dataset
- uspto-grants-1988_03
- Patent number
- US04728647
Reaction notes
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