Potassium Carbonate → 4-amino-5-chloro-2-methoxy-N-(1-(4-(2-naphthoylamino)butyl)piperidin-4-ylmethyl)benzamide

HRID 344314Notes

Reaction equation

HRID 344314 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(=O)([O-])[O-].[K+].[K+].[CH:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][C:33]=1[C:42](Cl)=[O:43]>ClCCl>[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:42]([C:33]3[CH:34]=[CH:35][C:36]4[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH:32]=3)=[O:43])[CH2:14][CH2:15]2)=[O:7])=[C:4]([O:24][CH3:25])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 752462-Naphthoyl chlorideHCID 541388784-amino-N-(1-(4-aminobutyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide

Product 1

HCID 537667874-amino-5-chloro-2-methoxy-N-(1-(4-(2-naphthoylamino)butyl)piperidin-4-ylmethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Amino-N-(1-(4-aminobutyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide (1.10 g) was dissolved in dichloromethane (30 ml), and potassium carbonate (0.82 g) was added. Then, a solution of 2-naphthoyl chloride (0.33 ml) in methylene chloride was dropwise added under ice-cooling. The mixture was stirred at room temperature for 1 hr, and the insoluble matter was filtered off. The filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography to give 0.25 g of 4-amino-5-chloro-2-methoxy-N-(1-(4-(2-naphthoylamino)butyl)piperidin-4-ylmethyl)benzamide.

Workup

  1. temperaturecooling
  2. filtrationthe insoluble 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-54aa6eeb9932432395e5bf258a80f963
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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