Benzoic Acid → 4-amino-N-(1-(4-benzoylaminobutyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide

HRID 344312Notes

Reaction equation

HRID 344312 reaction equation
[NH2:1][C:2]1[C:22]([Cl:23])=[CH:21][C:5]([C:6]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[CH2:12][CH2:11]2)=[O:7])=[C:4]([O:24][CH3:25])[CH:3]=1.[C:26](O)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[NH2:1][C:2]1[C:22]([Cl:23])=[CH:21][C:5]([C:6]([NH:8][CH2:9][CH:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:26](=[O:33])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:14][CH2:15]2)=[O:7])=[C:4]([O:24][CH3:25])[CH:3]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 541388784-amino-N-(1-(4-aminobutyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide

Product 1

HCID 106958104-amino-N-(1-(4-benzoylaminobutyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamideYield 20.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Amino-N-(1-(4-aminobutyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide (0.8 g) was dissolved in dimethylformamide (10 ml), and benzoic acid (0.25 g) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (0.44 g) were added. The mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure. Aqueous potassium carbonate solution was added to the residue and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography to give 0.2 g of 4-amino-N-(1-(4-benzoylaminobutyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionAqueous potassium carbonate solution was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-2ac0a2717cf243bdb177db2fa5b556f6
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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