Triethylamine → HCID 22923719, compound

HRID 1720302Notes

Reaction equation

HRID 1720302 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][S:17](Cl)(=[O:19])=[O:18])[CH:8]=2)[N:3]=1.[Cl:21][C:22]1[CH:41]=[CH:40][CH:39]=[CH:38][C:23]=1[CH2:24][NH:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][CH:31]([O:34][CH2:35][O:36][CH3:37])[CH2:30][CH2:29]1.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][S:17]([N:25]([CH2:24][C:23]3[CH:38]=[CH:39][CH:40]=[CH:41][C:22]=3[Cl:21])[CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][CH:31]([O:34][CH2:35][O:36][CH3:37])[CH2:30][CH2:29]3)(=[O:19])=[O:18])[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22923709HCID 22923709, compoundHCID 22923720HCID 22923720, compound

Product 1

HCID 22923719HCID 22923719, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.75 g of 4-(2-chloro-6-quinolyloxy)butylsulfonyl chloride was added, at 0° C., to a solution of 1.6 g of 1-[2-(2-chlorobenzylamino)ethyl]-4-methoxymethoxypiperidine and 1 ml of triethylamine in 25 ml dichloromethane. The mixture was stirred at room temperature for 1 day. The reaction mixture was washed with water and dried with magnesium sulfate. The solvent was removed by distillation. The resulting residue was purified by a silica gel column chromatography (eluant: 3% methanol/dichloromethane) to obtain 2.63 g of 2-chloro-6-[4-{N-(2-chlorobenzyl)-N-[2-(4-methoxymethoxy-1-piperidinyl)ethyl]aminosulfonyl}butoxy]quinoline.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried with magnesium sulfate
  3. customThe solvent was removed by distillation
  4. customThe resulting residue was purified by a silica gel column chromatography (eluant: 3% methanol/dichloromethane)

Sources & evidence

ORD record
ord-99584ecd219049688bebac38992ce038
Source dataset
uspto-grants-1996_04
Patent number
US05506239

Reaction notes

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