Methylamine → HCID 68744460, compound

Participants

Reaction Steps

5-(3-(hexyloxy)phenoxy)pentanal (72 mg, 0.26 mmol) in 1,2-C12C2H4 (5 mL) was treated with a THF solution of MeNH2 (2.0 M, 0.4 mL, 0.8 mmol). The reaction was stirred in a sealed vial for several min at rt before NaBH(OAc)3 (76 mg, 0.36 mmol) was added in one portion. Again the vial was sealed and stirred at rt for 3 d. The reaction was diluted with H2O and extracted into DCM. The organic extracts were concentrated and the resulting material was purified by preparative TLC on silica gel (5% MeOH:DCM) to afford the title compound as clear oil (17 mg, 23%). 1H NMR (400 MHz, CDCl3) δ ppm 7.15 (t, J=8.21 Hz, 1 H), 6.44-6.51 (m, 3 H), 3.90-3.98 (m, 4 H), 2.64 (t, J=7.07 Hz, 2 H), 2.46 (s, 3 H), 2.28 (br. s, 1 H), 1.72-1.85 (m, 4 H), 1.40-1.67 (m, 6 H), 1.29-1.40 (m, 4 H), 0.91 (t, J=6.57 Hz, 3 H). MS ESI [M+H]+, calcd for [C18H31NO2+H]+: 294.45 found m/z 294.2 (100).

Provenance & Evidence