Heptane → [4-(4-Methylpiperazine-1-carbonyl)phenyl]methanol

To a solution of N-methyl piperazine (3.33 ml, 30.09 mmol) was added a solution of trimethylaluminium in heptane (15.04 ml, 30.09 mmol) and the mixture was stirred 10 min at room temperature. To this solution was added a solution of 4-(hydroxymethyl)benzoic acid methyl ester (1000 mg, 6.02 mmol) in DCE and the mixture was refluxed under inert atmosphere for 3 h. The mixture was diluted with DCM then water was added. The suspension was filtered through celite. The filtrate was washed with a solution 5% of NaHCO3 (2×) then water and brine. The organic layers were dried over MgSO4, evaporated and dried at 40° C. under vacuum to afford 307 mg (Y=21%) of the title compound as an oil. 1H NMR (DMSO-d6) δ 7.45-7.37 (m, 4H), 5.33 (t, J=5.6 Hz, 1H), 4.58 (br d, 2H), 3.77-3.50 (m, 4H), 2.46-2.30 (m, 4H), 2.26 (s, 3H).

1. temperaturethe mixture was refluxed under inert atmosphere for 3 h
2. filtrationThe suspension was filtered through celite
3. washThe filtrate was washed with a solution 5% of NaHCO3 (2×)
4. dry with materialThe organic layers were dried over MgSO4
5. customevaporated
6. customdried at 40° C. under vacuum

ORD record

ord-285d4dda2a024ce9a6fd5ad7c467ef4d

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07838522B2