1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 14877443, compound

HRID 1608192Notes

Reaction equation

[C:1]([NH:4][C:5]1[C:13]([Cl:14])=[CH:12][C:8]([C:9]([OH:11])=O)=[C:7]([O:15][CH2:16][CH3:17])[CH:6]=1)(=[O:3])[CH3:2].[NH2:18][CH2:19][CH:20]1[O:25][CH2:24][CH2:23][N:22]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[CH2:21]1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[C:1]([NH:4][C:5]1[C:13]([Cl:14])=[CH:12][C:8]([C:9]([NH:18][CH2:19][CH:20]2[O:25][CH2:24][CH2:23][N:22]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH2:21]2)=[O:11])=[C:7]([O:15][CH2:16][CH3:17])[CH:6]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirred mixture of 4-acetylamino-5-chloro-2-ethoxybenzoic acid (2.0 g), 2-aminomethyl-4-(4-fluorobenzyl)morpholine (1.6 g), and dichloromethane (20 ml) is added 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.5 g), and the resulting mixture is stirred at 25° C. for 1.5 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. The residue is recrystallized from ethanol to give the title compound (2.1 g), mp 161°-163° C.

Workup

washThe reaction mixture is washed successively with water, aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
customevaporated
customThe residue is recrystallized from ethanol

Sources & evidence

ORD record: ord-0212490c51fb4e3fba89f14723e2a04e
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04870074

Reaction notes

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