N-(3-Aminopropyl)morpholine → HCID 55065471, compound

Participants

Reaction Steps

To 2,4-dichloropyrimidine (5.0 g, 33.5 mmol), diisopropylethylamine (5.85 ml, 33.5 mmol) in 50 mL of a 1:1 mixture of n-BuOH—H2O (1:1) is added 3-morpholinopropan-1-amine (4.90 mL, 33.5 mmol). The resulting mixture is stirred for 18 hours at room temperature. The mixture is then concentrated in vacuo, diluted with 30 mL H2O and extracted with EtOAc (3×75 mL). Combined organic layers are washed with saturated aqueous NaHCO3 (2×75 mL), saturated aqueous NaCl (2×75 mL), and dried (MgSO4). The residue is purified over silica (25% EtOAc in hexanes) to afford 4.5 g (53% yield) of the desired compound. 1H NMR (CDCl3, 300 MHz): δ 1.81 (m, 2H), 2.43-2.62 (m, 6H), 3.30 (m, 2H), 3.79-3.94 (m, 4H), 6.23 (d, J=5.4 Hz, 1H), 6.92 (bs, 1H), 7.99 (bs, 1H). MS (ESI, pos. ion) m/z: 257 (M+1).

Provenance & Evidence