Triethylamine → Mosapride

HRID 1608188Notes

Reaction equation

[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:12][CH2:13][CH3:14])[CH:3]=1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[NH2:30][CH2:31][CH:32]1[O:37][CH2:36][CH2:35][N:34]([CH2:38][C:39]2[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=2)[CH2:33]1>ClCCl>[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([NH:30][CH2:31][CH:32]2[O:37][CH2:36][CH2:35][N:34]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)[CH2:33]2)=[O:8])=[C:4]([O:12][CH2:13][CH3:14])[CH:3]=1

Participants

Conditions

Temperature: -10 °C

Procedure

To a stirred suspension of 4-amino-5-chloro-2-ethoxybenzoic acid (2.9 g) in dichloromethane (50 ml), triethylamine (1.6 g) is added at 25° C. The resulting mixture is cooled to -10° C., and isobutyl chloroformate (2.0 g) is added slowly. After the mixture is stirred at the same temperature for 1 hour, a solution of 2-aminomethyl-4-(4-fluorobenzyl)morpholine (3.0 g) in dichloromethane (10 ml) is added. The reaction mixture is stirred for 1 hour at a temperature of between -10° C. and -5° C. and then at 25° C. overnight. The mixture is washed successively with water, 10% aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and evaporated under reduced pressure. The residue is recyrstallized from ethanol to give the title compound (4.1 g), mp 151°-153° C.

Workup

additionis added at 25° C
stirringThe reaction mixture is stirred for 1 hour at a temperature of between -10° C. and -5° C.
customat 25° C.
customovernight
washThe mixture is washed successively with water, 10% aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-138022e7f82d469686cb14aadee064ee
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04870074

Reaction notes

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