Acetic Acid → HCID 13520146, compound

Participants

Reaction Steps

To a stirred solution of 1.4 g of the product aniline of Example 31 and 2.5 ml of 37% aqueous formaldehyde in 19 ml of acetonitrile was added in portions 0.62 g of sodium cyanoborohydride. After twenty minutes the solution was adjusted to pH 7 with glacial acetic acid and stirred for another hour. Ice was added, acetonitrile was removed in vacuo, and the mixture was partitioned between water and dichloromethane. The organic layer was dried over potassium carbonate, filtered, and concentrated to an oil which was chromatographed on a silica gel column using dichloromethane as eluent. Fractions containing the title compound were concentrated to give a solid, m.p. 159°-161°. Structure assignment was supported by the nmr spectrum and by elemental analysis.

Provenance & Evidence