p-Toluenesulfonic acid monohydrate → HCID 68525946, compound

HRID 1932499Notes

Reaction equation

HRID 1932499 reaction equation
O1CCCCC1[O:7][C:8]1[CH:33]=[CH:32][C:11]([CH2:12][NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([CH2:22][C:23]3[CH:31]=[CH:30][C:29]4[O:28][CH2:27][O:26][C:25]=4[CH:24]=3)[CH2:18][CH2:17]2)=[O:15])=[CH:10][CH:9]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:7][C:8]1[CH:33]=[CH:32][C:11]([CH2:12][NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([CH2:22][C:23]3[CH:31]=[CH:30][C:29]4[O:28][CH2:27][O:26][C:25]=4[CH:24]=3)[CH2:18][CH2:17]2)=[O:15])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 68523162HCID 68523162, compound

Product 1

HCID 68525946HCID 68525946, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-piperonylpiperazine-1-carboxylic acid 4-(tetrahydropyran-2-yloxy)benzylamide (1.1 g, 2.43 mmol) in methanol (50 mL) was added p-toluenesulfonic acid monohydrate (1.0 g, 5.26 mmol), and the resulting solution was stirred for 1 hour at room temperature. The resulting reaction solution was concentrated under reduced pressure. Water was added to the residue, and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and evaporated, to thereby yield 330 mg of the title compound.

Workup

  1. customThe resulting reaction solution
  2. concentrationwas concentrated under reduced pressure
  3. additionWater was added to the residue
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine
  6. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-f16fed0595e9406aa2270fe24bd4c413
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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