Benzaldehyde → HCID 53784190, compound

Temperature

0 °C

To N-methyl-5-dimethylamino-2-phenylpentanamide (5.0 g, 0.023 mol) dissolved in 50 ml THF was added 18.1 ml of a 2.5M solution of n-BuLi in n-hexane with ice-cooling under N2. After stirring at 0° C. for 30 min, benzaldehyde (2.4 g, 0.023 mol) dissolved in 10 ml THF was added dropwise to the foregoing solution. The reaction mixture was stirred for 5 min at 0° C. and then poured into ice-cold HCl. The resulting solution was washed with Et2O, basified by adding dilute NaOH while stirring in the cold, and extracted with CHCl3. The CHCl3 extract were combined, dried (Na2SO4), and evaporated Chromatography of the post-evaporation residue afforded the desired compound as a mixture of diastereoisomers as an oil. Dissolution in EtOH, acidification with HCl, followed by addition of Et2O gave the hydrochloride salt as a colorless solid. [Anal. Calc'd for C21H28N2O2.HCl.1/4EtOH: C, 66.17; H, 7.93; N, 7.18; Cl, 9.08. Found: C, 65.82; H, 8.02; N, 7.04; Cl 10.27.]

1. temperaturecooling under N2
2. additionwas added dropwise to the foregoing solution
3. stirringThe reaction mixture was stirred for 5 min at 0° C.
4. additionpoured into ice-cold HCl
5. washThe resulting solution was washed with Et2O
6. additionby adding dilute NaOH
7. stirringwhile stirring in the cold, and
8. extractionextracted with CHCl3
9. extractionThe CHCl3 extract
10. dry with materialdried (Na2SO4)
11. customevaporated Chromatography of the post-evaporation residue

ORD record

ord-33bea471c39f43e192099785b580ade6

Source dataset

uspto-grants-1989_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04847301