Benzoyl chloride → 4-amino-N-(1-(3-benzoylaminopropyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide

HRID 344383Notes

Reaction equation

HRID 344383 reaction equation
[NH2:1][C:2]1[C:21]([Cl:22])=[CH:20][C:5]([C:6]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][NH2:19])[CH2:12][CH2:11]2)=[O:7])=[C:4]([O:23][CH3:24])[CH:3]=1.C(N(CC)CC)C.[C:32](Cl)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C)C=O.C(Cl)Cl>[NH2:1][C:2]1[C:21]([Cl:22])=[CH:20][C:5]([C:6]([NH:8][CH2:9][CH:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][NH:19][C:32](=[O:39])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:14][CH2:15]2)=[O:7])=[C:4]([O:23][CH3:24])[CH:3]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 538956644-Amino-N-(1-(3-aminopropyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide

Product 1

HCID 106952284-amino-N-(1-(3-benzoylaminopropyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

4-Amino-N-(1-(3-aminopropyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide (0.70 g) was dissolved in dimethylformamide (10 ml). Triethylamine (0.30 ml) was added, and a solution of benzoyl chloride (0.25 ml) in methylene chloride was dropwise added under ice-cooling. The mixture was stirred at room temperature. Insoluble matter was filtered off and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography to give 0.15 g of 4-amino-N-(1-(3-benzoylaminopropyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide.

Workup

  1. temperaturecooling
  2. filtrationInsoluble matter was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-169e45f222b74e70b8bff77998e36193
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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