Benzenesulfonyl chloride → 4-amino-N-(1-(4-benzenesulfonylaminobutyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide

HRID 344384Notes

Reaction equation

HRID 344384 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(N(CC)CC)C.[C:33]1([S:39](Cl)(=[O:41])=[O:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>ClCCl.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][S:39]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)(=[O:41])=[O:40])[CH2:14][CH2:15]2)=[O:7])=[C:4]([O:24][CH3:25])[CH:3]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 541388784-amino-N-(1-(4-aminobutyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide

Product 1

HCID 541168134-amino-N-(1-(4-benzenesulfonylaminobutyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

4-Amino-N-(1-(4-aminobutyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide (1.00 g) was dissolved in a mixed solvent of dichloromethane (20 ml) and dimethylformamide (15 ml). Triethylamine (0.57 ml) was added, and a solution of benzenesulfonyl chloride (0.35 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 0.57 g of 4-amino-N-(1-(4-benzenesulfonylaminobutyl)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-461ee6e32ad24d578c1eecd69eaa363c
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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