Methylamine → HCID 11839004, compound

At 0° C., 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (14.2 g, 74.2 mmol) was added to a solution of (1-naphthyloxy)acetic acid (15.0 g, 74.2 mmol) and 1-hydroxybenzotriazole (10.0 g, 74.2 mmol) in DCM (100 ml) and N,N-dimethylformamide (100 ml). The reaction mixture was stirred for 30 min at this temperature. A 8.0 M solution of methylamine (185 ml, 1.4 mol) was added. The reaction mixture was stirred for 16 hours, while it was warming up to room temperature. It was diluted with ethyl acetate (300 ml) and washed with a 10% aqueous solution of sodium hydrogen sulphate (2×300 ml). The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate (400 ml) and dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (300 g), using ethyl acetate/heptane as eluent, to give 17.44 g of N-methyl-2-(1-naphthyloxy)acetamide.

1. stirringThe reaction mixture was stirred for 16 hours, while it
2. washwashed with a 10% aqueous solution of sodium hydrogen sulphate (2×300 ml)
3. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate (400 ml)
4. dry with materialdried over magnesium sulphate
5. customThe solvent was removed in vacuo
6. customThe crude product was purified by flash chromatography on silica (300 g)

ORD record

ord-39591c6173584b3aa0b58bc1a7ca1699

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06437147B1