p-Toluenesulfonic acid → 6-(5-Methylthiophen-2-yl)-5-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)naphthalen-2-ol 4-methylbenzenesulfonate

HRID 445203Notes

Reaction equation

HRID 445203 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[C:8]([O:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:21][CH:20]=3)=[C:9]3[C:14](=[CH:15][CH:16]=2)[CH:13]=[C:12]([OH:17])[CH:11]=[CH:10]3)=[CH:4][CH:3]=1.C(OCC)(=O)C.[C:40]1([CH3:50])[CH:45]=[CH:44][C:43]([S:46]([OH:49])(=[O:48])=[O:47])=[CH:42][CH:41]=1>O1CCCC1>[CH3:1][C:2]1[S:6][C:5]([C:7]2[C:8]([O:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:21][CH:20]=3)=[C:9]3[C:14](=[CH:15][CH:16]=2)[CH:13]=[C:12]([OH:17])[CH:11]=[CH:10]3)=[CH:4][CH:3]=1.[CH3:50][C:40]1[CH:41]=[CH:42][C:43]([S:46]([O-:49])(=[O:48])=[O:47])=[CH:44][CH:45]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 451026266-(5-Methylthiophen-2-yl)-5-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)naphthalen-2-ol

Product 1

HCID 1317306756-(5-Methylthiophen-2-yl)-5-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)naphthalen-2-ol 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Place 6-(5-methylthiophen-2-yl)-5-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)naphthalen-2-ol (103.4 mg, 0.22 mmol) in a vial. Add ethyl acetate (4 mL) and p-toluenesulfonic acid (52 mg, 0.30 mmol) and stir at ˜60° C. Add tetrahydrofuran to clarify the solution and sonicate for 15 minutes. Carefully decant the suspension from gum that forms on the flask. Filter the suspension to obtain a cake of very light pink solids. Wash the cake with pentane (2×2 mL) and dry in a 40° C. vacuum oven overnight to obtain the title compound. MP (DSC)=136.24° C.

Workup

  1. customsonicate for 15 minutes
  2. customCarefully decant the suspension from gum that
  3. filtrationFilter the suspension
  4. customto obtain a cake of very light pink solids
  5. washWash the cake with pentane (2×2 mL)
  6. customdry in a 40° C. vacuum oven overnight

Sources & evidence

ORD record
ord-212d12b254a0431b8462c843a087229a
Source dataset
uspto-grants-2013_07
Patent number
US08476300B2

Reaction notes

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