Reaction #3869

Reaction equation

piperidine

product

7-Methoxy-3-hydroxy-2,2-dimethylbenzofuran

sodium bicarbonate

Methanesulfonyl chloride

→

desired product

7-Methoxy-3-piperidino-2,2-dimethylbenzofuran

Solvents

methylene chloride

Triethylamine

Conditions

Workup

1. 1
   Otherat RT
2. 2
   Temperaturecooled to 0° C.
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITcontinued at RT overnight
5. 5
   Otherthe phases separated
6. 6
   Washthe organic phase washed with sodium bicarbonate
7. 7
   Otherdried
8. 8
   Filtrationfiltered
9. 9
   Otherevaporated in vacuo
10. 10
    workup.DISSOLUTIONThe residue is dissolved in toluene
11. 11
    Otherevaporated in vacuo

Procedure

Triethylamine (29 ml) is added to a stirred solution of the product obtained in Step 4. (25.4 g) in methylene chloride (560 ml) at RT under nitrogen. Methanesulfonyl chloride (11.1 ml) is added dropwise to the mixture which is cooled to 0° C. The mixture is stirred for 3 hours at RT, cooled to 0° C., piperidine (128 ml) added and stirring continued at RT overnight. Sat'd aq. sodium bicarbonate is added to the mixture, the phases separated and the organic phase washed with sodium bicarbonate, sat'd NACl, dried, filtered and evaporated in vacuo. The residue is dissolved in toluene and evaporated in vacuo affording the desired product as the hydrochloride salt.

Source