Thionyl Chloride → HCID 178471784, compound

Participants

Reaction Steps

Thionyl chloride (470 mg, 288 μL, 3-95 mmol) was added to a stirred solution of ethyl [trans-4-({ethyl[2-(hydroxymethyl)pyridin-3-yl]amino}methyl)cyclohexyl]acetate (132.2 mg, 0.395 mmol) in dry CH2Cl2 (10 mL) at room temperature. The reaction was stirred overnight at room temperature then quenched with pyridine (425 μL) and washed with water. The aqueous layer was extracted with CH2Cl2 (2×20 mL) an the combined extracts were dried (Na2SO4) and concentrated in vacuo to afford ethyl (trans-4-{[[2-(chloromethyl)pyridin-3-yl](ethyl)amino]methyl}cyclohexyl)acetate. 1H NMR (500 MHz, CDCl3): δ 8.37 (dd, J=1.2, 4.5 Hz, 1 H); 7.51 (dd, J=1.4, 8.1 Hz, 1 H); 7.23 (dd, J 3.7, 8.3 Hz, 1 H); 4.86 (s, 2 H); 4.10 (q, J=7.1 Hz, 2 H); 3.03 (q, J=7.1 Hz, 2 H); 2.81 (d, J=7.1 Hz, 2 H); 2.14 (d, J=6.8 Hz, 2 H); 1.80-1.67 (m, 5 H); 1.42-1.29 (m, 1 H); 1.23 (t, J=7.1 Hz, 3 H); 0.99 (t, J=7.1 Hz, 3H); 0.94-0.86 (m, 4 H).

Provenance & Evidence