Triethylamine → HCID 22923700, compound

HRID 1720309Notes

Reaction equation

HRID 1720309 reaction equation
[CH3:1][O:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][NH:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[NH:25][C:24](=[O:29])[CH:23]=[CH:22]3)[CH2:7][CH2:6]1.[CH:30]1([CH2:36][S:37](Cl)(=[O:39])=[O:38])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.C(N(CC)CC)C>ClCCl>[CH3:1][O:2][CH2:3][O:4][CH:5]1[CH2:6][CH2:7][N:8]([CH2:11][CH2:12][N:13]([CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[NH:25][C:24](=[O:29])[CH:23]=[CH:22]3)[S:37]([CH2:36][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)(=[O:39])=[O:38])[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3871475Cyclohexylmethane sulfonyl chlorideHCID 22923686HCID 22923686, compound

Product 1

HCID 22923700HCID 22923700, compoundYield 17.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.5 g of 6-{4-[2-(4-methoxymethoxy-1-piperidinyl)ethyl]aminobutoxy}carbostyril, 1.5 g of cyclohexylmethanesulfonyl chloride and 1.35 ml of triethylamine in 30 ml of dichloromethane was stirred at room temperature for 16 hours. 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/chloroform)-to obtain 620 mg of 6-[4-{N-[2-(4-methoxymethoxy-1-piperidinyl)ethyl]-N-cyclohexylmethylsulfonylamino}butoxy]carbostyril.

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/chloroform)

Sources & evidence

ORD record
ord-59cf83b8948f4b2c84d339f5ac1fdd61
Source dataset
uspto-grants-1996_04
Patent number
US05506239

Reaction notes

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