Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 68500417, compound

HRID 1176415Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][C:5]([N:7]([CH3:23])[C:8]1[CH:13]=[C:12]([CH2:14][O:15]C2CCCCO2)[CH:11]=[CH:10][C:9]=1[CH3:22])=[O:6].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[OH:15][CH2:14][C:12]1[CH:11]=[CH:10][C:9]([CH3:22])=[C:8]([N:7]([CH3:23])[C:5](=[O:6])[CH2:4][CH2:3][O:2][CH3:1])[CH:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

The solution of 4.50 g of 3-methoxy-N-methyl-N-[2-methyl-5-(tetrahydropyran-2-yloxymethyl)phenyl]propionamide in 70 ml of ethanol is admixed with 0.350 g of pyridinium p-toluenesulphonate and stirred at 60° C. over 2 hours. The reaction mixture is cooled and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.15 (3:1 EtOAc-heptane); Rt=2.60.

Workup

temperatureThe reaction mixture is cooled
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-746ad90fec964e068261af6e7242e37c
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842688B2

Reaction notes

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