1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 4-amino-N-[(4-benzyl-2-morpholinyl)methyl]-5-chloro-2-hydroxybenzamide

HRID 1608201Notes

Reaction equation

HRID 1608201 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][CH:13]=[CH:12][CH:11]=2)[CH2:4]1.C([O:19][C:20]1[CH:28]=[C:27]([NH:29]C(=O)C)[C:26]([Cl:33])=[CH:25][C:21]=1[C:22](O)=[O:23])(=O)C.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[NH2:29][C:27]1[C:26]([Cl:33])=[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][CH:13]=[CH:12][CH:11]=3)[CH2:4]2)=[O:23])=[C:20]([OH:19])[CH:28]=1

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2776360(4-Benzylmorpholin-2-yl)methanamineHCID 198486102-Acetoxy 4-acetamino 5-chlorobenzoic acid

Product 1

HCID 148819784-amino-N-[(4-benzyl-2-morpholinyl)methyl]-5-chloro-2-hydroxybenzamideYield 54.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of 2-aminomethyl-4-benzylmorpholine (3.1 g), 2-acetoxy-4-acetylamino-5-chlorobenzoic acid (4.0 g), and dichloromethane (40 ml) is added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.9 g), and the mixture is stirred at 25° C. for 4 hours. The reaction mixture is washed successively with water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and evaporated under reduced pressure. The residue is dissolved in ethanol (80 ml), and 10% hydrochloric acid (30 ml) is added. The mixture is refluxed with stirring for 2 hours and concentrated under reduced pressure. The residue is neutralized with aqueous sodium bicarbonate solution and extracted with chloroform. The organic layer is washed successively with water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and evaporated under reduced pressure. The residue is recrystallized from isopropyl alcohol to give the monohydrate of the title compound (3.0 g), mp 153°-155° C.

Workup

  1. washThe reaction mixture is washed successively with water and saturated aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. dissolutionThe residue is dissolved in ethanol (80 ml)
  5. addition10% hydrochloric acid (30 ml) is added
  6. temperatureThe mixture is refluxed
  7. stirringwith stirring for 2 hours
  8. concentrationconcentrated under reduced pressure
  9. extractionextracted with chloroform
  10. washThe organic layer is washed successively with water and saturated aqueous sodium chloride solution
  11. dry with materialdried over magnesium sulfate
  12. customevaporated under reduced pressure
  13. customThe residue is recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-eb9b7fad51c3452fae30ef1de43531c4
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

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