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

HRID 1608192
Notes
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Reaction equation

HRID 1608192 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 102427352-Aminomethyl-4-(4-fluorobenzyl)morpholineHCID 148773904-(Acetylamino)-5-chloro-2-ethoxybenzoic acid

Product 1

HCID 14877443HCID 14877443, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

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

  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
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes