4-Toluenesulfonyl chloride → HCID 86709390, compound

HRID 2172240Notes

Reaction equation

HRID 2172240 reaction equation
[CH3:1][C:2]([OH:33])([CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=3)[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)[CH2:3][CH2:4][OH:5].C(N(CC)CC)C.[C:41]1([CH3:51])[CH:46]=[CH:45][C:44]([S:47](Cl)(=[O:49])=[O:48])=[CH:43][CH:42]=1>ClCCl>[OH:33][C:2]([CH3:1])([CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:15][CH2:16][CH:17]([CH2:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]([O:28][C:29]([F:32])([F:30])[F:31])=[CH:26][CH:27]=3)[CH2:18][CH2:19]2)=[CH:12][CH:13]=1)[CH2:3][CH2:4][O:5][S:47]([C:44]1[CH:45]=[CH:46][C:41]([CH3:51])=[CH:42][CH:43]=1)(=[O:49])=[O:48]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 70874234HCID 70874234, compound

Product 1

HCID 86709390HCID 86709390, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Methyl-4-(4-{4-[2-(4-trifluoromethoxyphenyl)ethyl]piperidin-1-yl}phenoxy)butane-1,3-diol (1.68 g, 3.6 mmol), dichloromethane (17 ml), triethylamine (1.00 ml, 7.2 mmol) and p-toluenesulfonyl chloride (0.82 g, 4.3 mmol) were mixed and ice-cooled. 1,1,3,3,-Tetramethylpropanediamine (0.12 ml, 0.7 mmol) was added thereto and stirred at room temperature for 1 hour. The reaction mixture was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The organic layer was concentrated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0, 50:50) to afford the title compound as a colorless powder (2.03 g, 91%).

Workup

  1. temperatureice-cooled
  2. washThe reaction mixture was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over sodium sulfate
  4. concentrationThe organic layer was concentrated
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0, 50:50)

Sources & evidence

ORD record
ord-dcf7b05d23c14b648926d2e358f0b7c0
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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