1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 19848625, compound

HRID 1608195Notes

Reaction equation

[NH2:1][CH2:2][CH:3]1[O:8][CH:7]([CH3:9])[CH2:6][N:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[CH2:4]1.[NH2:18][C:19]1[C:27]([Cl:28])=[CH:26][C:22]([C:23](O)=[O:24])=[C:21]([O:29][CH2:30][CH3:31])[CH:20]=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[NH2:18][C:19]1[C:27]([Cl:28])=[CH:26][C:22]([C:23]([NH:1][CH2:2][CH:3]2[O:8][CH:7]([CH3:9])[CH2:6][N:5]([CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[CH2:4]2)=[O:24])=[C:21]([O:29][CH2:30][CH3:31])[CH:20]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 2-aminomethyl-4-(2-chlorobenzyl)-6-methylmorpholine (2.2 g) in dichloromethane (50 ml), 4-amino-5-chloro-2-ethoxybenzoic acid (1.9 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.7 g) are added. The reaction mixture is stirred at 25° C. for 4 hours, washed successively with water, aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution, and dried over magnesium sulfate. The solvent is distilled off under reduced pressure, and the residue is chromatographed on silica gel with ethyl acetate-hexanechloroform (1:1:1) to give the title compound (2.6 g) as an oil.

Workup

washwashed successively with water, aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
distillationThe solvent is distilled off under reduced pressure
customthe residue is chromatographed on silica gel with ethyl acetate-hexanechloroform (1:1:1)

Sources & evidence

ORD record: ord-95de7eb35e774e099fd55593746543c0
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04870074

Reaction notes

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