Dimethylamine, hydrochloride → HCID 586061, compound

Participants

Reaction Steps

To a stirred suspension of 2-((4-methoxyphenyl)amino)acetic acid (18) (45 g, 0.25 mol) and dimethylamine hydrochloride (40.5 g, 0.5 mol) in acetonitrile (1 L) at 0° C., was added DIPEA (174 ml, 0.99 mol) followed by HATU (99 g, 0.26 mol). The reaction mixture was stirred at RT for 1 h, and then partitioned between EtOAc (1 L) and 5% NaH2PO4 (aq.) (250 mL), the organic layer was washed with sat. NaHCO3 (aq.) (3×300 mL), and 3M HCl (aq.) (4×250 mL). The combined acidic extracts were cooled to 0° C. and solid NaOH was added to pH 14 and the aqueous phase was extracted with EtOAc (3×400 mL), the combined organics were washed with brine (500 mL) dried (MgSO4), filtered and solvents removed in vacuo to give 2-((4-methoxyphenyl)amino)-N,N-dimethylacetamide (19) (37.1 g, 71%) as a brown solid: m/z 209 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 6.74-6.70 (m, 2H), 6.65-6.59 (m, 2H), 5.10 (br s, 1H), 3.81 (s, 2H), 3.64 (s, 3H), 3.01 (s, 3H), 2.87 (s, 3H).

Provenance & Evidence