4-(3-Bromopropyl)morpholine → 7-(3-Morpholinopropoxy)naphthalene-2-sulfonic acid

Participants

Reaction Steps

Following a procedure analogous to that for the synthesis of Intermediate 26B, sodium 7-oxidonaphthalene-2-sulfonate (Pfaltz and Bauer, 200 mg, 0.75 mmol) and 4-(3-bromopropyl)morpholine (310 mg, 1.49 mmol) were converted to the title compound (180 mg, 69%). 1H NMR (DMSO-d6) δ 9.53 (br s, 1H), 8.06 (s, 1H), 7.82 (d, J=9.0 Hz, 1H), 7.77 (d, J=8.6 Hz, 1H), 7.73-7.68 (m, 1H), 7.55 (dd, J=8.4, 1.5 Hz, 1H), 7.40 (d, J=2.2 Hz, 1H), 4.20 (t, J=5.8 Hz, 2H), 4.00 (d, J=11.0 Hz, 2H), 3.65 (t, J=11.6 Hz, 2H), 3.51 (d, J=12.3 Hz, 2H), 3.37-3.32 (m, 2H), 3.17-3.07 (m, 2H), 2.23-2.16 (m, 2H); MS (ESI+) m/z 350.3 (M+H)+.

Provenance & Evidence