4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 2-(2-methyl-4-pyrrolidin-1-yl-quinolin-7-yloxy)-ethyl ester

HRID 2415495Notes

Reaction equation

HRID 2415495 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([O:17][CH2:18][CH2:19][OH:20])=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.[S:28](Cl)([C:31]1[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=1)(=[O:30])=[O:29].C([O-])(O)=O.[Na+]>ClCCl>[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[C:9]2[C:4](=[CH:5][C:6]([O:17][CH2:18][CH2:19][O:20][S:28]([C:31]3[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=3)(=[O:30])=[O:29])=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 22641504HCID 22641504, compound

Product 1

HCID 86586939Toluene-4-sulfonic acid 2-(2-methyl-4-pyrrolidin-1-yl-quinolin-7-yloxy)-ethyl esterYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of of 2-(2-methyl-4-pyrrolidin-1-yl-quinolin-7-yloxy)-ethanol (425 mg, 1.56 mmol) in dichloromethane (20 mL) was added triethylamine (0.9 mL, 6.49 mmol) and tosyl chloride (1115 mg, 5.85 mmol). The reaction mixture was stirred 22 h at room temperature. An aqueous solution of NaHCO3 was added. After separation, the organic layer was washed with brine. The brown gum was triturated with diethylether. After filtration, the solid was dried in a high vacuum to give 520 mg (78.1%) of toluene-4-sulfonic acid 2-(2-methyl-4-pyrrolidin-1-yl-quinolin-7-yloxy)-ethyl ester as a light yellow solid. ISP mass spectrum, m/e: 427.5 (M+1 calculated for C23H26N2O4S: 427.5).

Workup

  1. customAfter separation
  2. washthe organic layer was washed with brine
  3. customThe brown gum was triturated with diethylether
  4. filtrationAfter filtration
  5. customthe solid was dried in a high vacuum

Sources & evidence

ORD record
ord-4cee1e8be8514c10b8aff6fa71676768
Source dataset
uspto-grants-2004_11
Patent number
US06818767B2

Reaction notes

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