Isobutyryl chloride → HCID 178454416, compound

Participants

Reaction Steps

To a stirring solution of Example 111, (3-(4-Pyrrolidin-1-ylmethyl-phenyl)-cyclobutylmethyl]-piperazine) (100 mg, 0.32 mmol) in 1,2-dichloroethane (4 mL) was added diisopropyl ethylamine (111 uL, 0.64 mmol) followed by the addition of isobutyryl chloride (50 uL, 0.48 mmol). After 15 min the reaction was quenched with 1N NaOH, extracted with dichloromethane. The combined organic layers were dried over MgSO4, filtered through a fritted funnel and concentrated under reduced pressure. Purification of this material was accomplished by flash column chromatography, using a 12 g ISCO column, eluting with 4% MeOH/CH2Cl2 with 0.2% NH4OH. The product containing fractions were collected and concentrated to give the title compound (118 mg, 97% yield) as colorless oil. Rf=0.27 (10% MeOH/CH2Cl2 w/0.2% NH4OH); 500 MHz 1H NMR (CDCl3) δ 7.23 (d, J=8.3 Hz, 2H), 7.15 (d, J=8.3 Hz, 2H), 3.61–3.44 (m, 7H), 2.74 (septet, J=7.1 Hz, 1H), 2.56–2.45 (m, 7H), 2.42–2.34 (m, 4H), 2.28–2.20 (m, 2H), 2.17–2.09 (m, 2H), 1.79–1.70 (m, 4H), 1.08 (d, J=7.1 Hz, 6H); 125 MHz 13C NMR (CDCl3) δ 175.5, 145.1, 136.7, 129.1, 126.5, 64.3, 60.5, 54.3, 45.6, 41.8, 36.5, 33.4, 30.1, 29.0, 23.6, 19.6; LRMS m/z Calcd for C24H37N3O 383.6; obsd LRMS APCI (M+1) m/z 384.

Provenance & Evidence