Acetic Acid → Cyclopentyl-{4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetra-hydropyran-4-ylmethyl}amine

To a solution of (4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-yl}methylamine (254 mg, 0.798 mmol) in dichloroethane (5 mL) under nitrogen atmosphere were added acetic acid (37 mg, 1.6 mmol), triethylamine (97 mg, 1.6 mmol) and cyclopentanone (10 mg, 1.19 mmol). The mixture was stirred for 30 min at ambient temperature and NaHB(OAc)3 (204 mg, 1.6 mmol) was added at 0° C. After stirring overnight, the reaction mixture was filtered over celite, concentrated in vacuo and purified by column chromatography on silica gel eluting with DCM:MeOH:NH3 (89:10:1) to give the title compound (226 mg, 58%). 1H NMR (400 MHz, CDCl3) δ 7.20 (d, 2H), 6.88H), 4.03 (t, 2H), 3.78-3.73 (m, 2H), 3.59-3.53 (m, 2H), 2.84 (q, 1H), 2.73 (t, 2H), 2.65-2.68 (m, 6H), 2.03-2.12 (m, 4H), 1.84-1.94 (m, 6H), 1.65-1.72 (m, 2H), 1.51-1.58 (m, 2H), 1.41-1.46 (m, 2H), 1.07-1.16 (m, 2H).

1. stirringAfter stirring overnight
2. filtrationthe reaction mixture was filtered over celite
3. concentrationconcentrated in vacuo
4. custompurified by column chromatography on silica gel eluting with DCM:MeOH:NH3 (89:10:1)

ORD-Eintrag

ord-dcdaedf0558549bbb00d5f26f4ae75d4

Quelldatensatz

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07456164B2