Hydrochloric Acid → HCID 15456878, compound

Participants

Reaction Conditions

Reaction Steps

A solution of bis(4,4,5,5,6,6,7,7,7-nonafluoroheptyl)amine (3.0 g) and formic acid (90%, 1.5 g) was cooled in an ice-water bath and 8 ml of formaldehyde (37% weight) was added. The solution was slowly heated to 90° C. and maintained overnight. (Foaming and gas evolution at 60-75° C.) Concentrated hydrochloric acid (1 ml) was added and 7 ml of solution were removed by distillation. The remaining solution was cooled and treated with KOH (aq. 10%) to pH 11. The mixture was extracted with methylene chloride (3×50 ml). The combined methylene chloride extracts were washed with water (2×50 ml), dried over sodium sulfate, and concentrated on vacuum to give a residue. Distillation of the residue at reduced pressure gave 2.7 g of bis(4,4,5,5,6,6,7,7,7-nonafluoroheptyl)methylamine, yield 88%. 19F NMR (CDCl3) -81.7 (m, 6F), -115.1 (m, 4F), -125.1 (m, 4F), -126.6 (m, 4F) ppm. 1H NMR (CDCl3) 2.40 (t, J=6 Hz, 4H), 2.19 (s, 3H), 2.16 (m, 4H), 1.76 (m, 4H) ppm. 13C NMR (CDCl3) 18.4, 28.7 (t, J=23 Hz), 41.3, 56.5, 108-123 (m) ppm. MS (m/e) 532 (M+ -F, 7.5%), 382 (1.0%), 304 (100%), 195 (0.6%), 169 (0.8%), 119 (2.5%), 69 (9.4%).

Provenance & Evidence