6-Aminohexanoic Acid → Methyl 6-aminohexanoate

Participants

Reaction Steps

6-aminohexanoic acid (20 g, 0.15 mol) was suspended in methanol (80 mL), the mixture was cooled to −20° C. (acetone/dry ice) and thionyl chloride (14 mL, 0.2 mol) was added dropwise maintaining a temperature below −10° C. After addition of all thionyl chloride the cooling bath was removed and the mixture stirred for 90 minutes at room temperature. The mixture was refluxed shortly (5 minutes) and the solvents removed in vacuum. The residue was redissolved in methanol (60 mL). The product was precipitated by addition of diethyl ether (200 mL) with cooling on an ice bath. The product was collected by filtration as a white solid (22 g, 81%). The product was shown to be pure by TLC. R1(methanol)=0.13. Melting point 123-124° C. Mass spectroscopy (FAB+): 146.1 (MH+). 1H-NMR (DMSO-d6) δ: 8.1 (br. s, 3H), 3.60 (s, 3) 2.75 (t, 2H), 2.30 (t, 2H), 1.50 (qn, 4H), 1.30 (qn, 2H).

Provenance & Evidence