1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Mosapride

HRID 1608187Notes

Reaction equation

HRID 1608187 reaction equation
[NH2:1][CH2:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH2:4]1.[NH2:17][C:18]1[C:26]([Cl:27])=[CH:25][C:21]([C:22](O)=[O:23])=[C:20]([O:28][CH2:29][CH3:30])[CH:19]=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[NH2:17][C:18]1[C:26]([Cl:27])=[CH:25][C:21]([C:22]([NH:1][CH2:2][CH:3]2[O:8][CH2:7][CH2:6][N:5]([CH2:9][C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)[CH2:4]2)=[O:23])=[C:20]([O:28][CH2:29][CH3:30])[CH:19]=1

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 102427352-Aminomethyl-4-(4-fluorobenzyl)morpholineHCID 105366584-Amino-5-chloro-2-ethoxybenzoic acid

Product 1

HCID 119584MosaprideYield 63.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 2-aminomethyl-4-(4-fluorobenzyl)morpholine (2.5 g) in dichloromethane (50 ml), 4-amino-5-chloro-2-ethoxybenzoic acid (2.7 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.4 g) are added, and the mixture is stirred at 25° C. for 4 hours. The reaction mixture is washed successively with water, aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and evaporated under reduced pressure. The residue is recrystallized from ethanol to give the title compound (3.0 g), mp 151°-153° C.

Workup

  1. washThe reaction mixture is washed successively with water, aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-8f1e81abb3cd47bd95c481b5e714425b
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

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