Triethylamine → N-{1-(R)-[4-(3,4-dichlorobenzyl)piperazin-1-ylmethyl]-2-methylpropyl}-4-fluorobenzenesulfonamide

HRID 1250531Notes

Reaction equation

HRID 1250531 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1.Cl.Cl.[Cl:21][C:22]1[CH:23]=[C:24]([CH:47]=[CH:48][C:49]=1[Cl:50])[CH2:25][N:26]1[CH2:31][CH2:30][N:29]([CH2:32][C@@H:33]([NH:37]C(=O)C2C=CC(C)=CC=2)[CH:34]([CH3:36])[CH3:35])[CH2:28][CH2:27]1>C(Cl)Cl>[Cl:21][C:22]1[CH:23]=[C:24]([CH:47]=[CH:48][C:49]=1[Cl:50])[CH2:25][N:26]1[CH2:31][CH2:30][N:29]([CH2:32][C@H:33]([NH:37][S:15]([C:12]2[CH:13]=[CH:14][C:9]([F:8])=[CH:10][CH:11]=2)(=[O:17])=[O:16])[CH:34]([CH3:36])[CH3:35])[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 9958340n-{1 (s)-[4-(3,4-Dichlorobenzyl)piperazin-1-ylmethyl]-2-methylpropyl}-4-methylbenzamide dihydrochloride salt

Product 1

HCID 18346059N-{1-(R)-[4-(3,4-dichlorobenzyl)piperazin-1-ylmethyl]-2-methylpropyl}-4-fluorobenzenesulfonamideYield 66.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (21 ml, 0.15 mmol) and 4-fluorobenzenesulfonyl chloride (29 mg, 0.15 mmol) were added to a solution of 1-(R)-[4-(3,4-dichlorobenzyl)piperazin-1-ylmethyl]-2-methylpropylamine (50 mg, 0.15 mmol) [prepared as described in Example 1 above] in methylene chloride (1.5 ml). The reaction mixture was stirred for 2 h, then concentrated. Purification by flash chromatography with 20:1 methylene:methanol as the eluant gave N-{1-(R)-[4-(3,4-dichlorobenzyl)piperazin-1-ylmethyl]-2-methylpropyl}-4-fluorobenzenesulfonamide (49 mg) as a solid.

Workup

  1. concentrationconcentrated
  2. customPurification by flash chromatography with 20:1 methylene

Sources & evidence

ORD record
ord-e90abf2d1f934780b6688b2904f26fe2
Source dataset
uspto-grants-2002_01
Patent number
US06339087B1

Reaction notes

Loading…