Bromoacetic Acid → 4-Morpholineacetic acid

Participants

Reaction Steps

Bromoacetic acid (2g, 14.4 mole) was dissolved in tetrahydrofuran (50mL) and added dropwise to a stirred solution of morpholine (3.76g, 43.2 mole) in tetrahydrofuran (THF, 20mL). The solution was stirred at room temperature for three days. The white solid (4.17g) was filtered, washed with THF (100mL), and recrystallised from hot ethanol (EtOH), Yield: 2.59g: IR:1740cm-1. For the two different isobaric versions of morpholine acetic acid, either bromoacetic-1-13C acid (Aldrich PN 27,933-1) or bromoacetic-2-13C acid (Aldrich PN 27,935-8) was substituted for bromoacetic acid.

Provenance & Evidence