Reaction #3866

Reaction equation

Methane sulfonyl chloride

product

4-Hydroxy-8-methoxy-2,3-dihydrobenzopyran

triethylamine

piperidine

→

desired product

8-Methoxy-4-piperidino-2,3-dihydrobenzopyran

Solvents

methylene chloride

Conditions

Workup

1. 1
   workup.STIRRINGthe reaction mixture is stirred under nitrogen overnight
2. 2
   WashThe reaction mixture is washed with sat'd aq. sodium bicarbonate
3. 3
   Otherdried
4. 4
   Filtrationfiltered
5. 5
   Otherevaporated in vacuo

Procedure

Methane sulfonyl chloride (14.9 ml) is added dropwise to a solution of the product obtained in Step 1. (31.6 g) and triethylamine (29.3 ml) in methylene chloride (750 ml) cooled to 0° C. under nitrogen. The reaction mixture is stirred for 11/2 hours; piperidine (175 ml) is added and the reaction mixture is stirred under nitrogen overnight. The reaction mixture is washed with sat'd aq. sodium bicarbonate, sat'd NaCl, dried, filtered and evaporated in vacuo yielding the desired product as its hydrochloride salt.

Source