4-Toluenesulfonyl chloride → N,N-Dimethylfuro[3,2-c]pyridine-6-methanamine

To a solution of triethylamine (3.45 mL, 24.7 mmol) in methylene chloride (16 mL) under a nitrogen atmosphere and cooled below 5° C. was added p-toluenesulfonyl chloride (4.65 g, 24.4 mmol) in one portion. After stirring the mixture for 15 minutes, a solution of 6-hydroxymethylfuro[3,2-c]pyridine (2.68 g, 18 mmol) in methylene chloride (18 mL) was added dropwise. By tlc the reaction was complete in 6-8 hours. Dimethylamine gas was bubbled over the reaction surface until product formation was complete. The reaction solution was washed with water and the product extracted into dilute hydrochloric acid. The acidic aqueous extract was made basic with sodium hydroxide solution and the product extracted into diethyl ether. The ethereal solution was dried over anhydrous sodium sulfate, filtered through a pad of charcoal and evaporated to give an oil (1.76 g). The oil was distilled under vacuum to give 1.56 g (49% yield) of pure product, bp: 93°-94° C./1.6 mm Hg. Upon standing the product crystallized, mp: 42°-44° C.

1. waitwas complete in 6-8 hours
2. customDimethylamine gas was bubbled over the reaction surface until product formation
3. washThe reaction solution was washed with water
4. extractionthe product extracted into dilute hydrochloric acid
5. extractionThe acidic aqueous extract
6. extractionthe product extracted into diethyl ether
7. dry with materialThe ethereal solution was dried over anhydrous sodium sulfate
8. filtrationfiltered through a pad of charcoal
9. customevaporated

ORD record

ord-478dedd8064e4691ba3650f502a4a05c

Source dataset

uspto-grants-1989_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04808595