Acetic Acid → HCID 17770045, compound

Temperature

40 °C

A 250-mL round-bottomed flask was charged with a solution of 9-(3-(dimethylamino)propyl)-9H-carbazole-3-carbaldehyde (800 mg, 2.86 mmol, 1.00 equiv) in EtOH (120 mL), tert-butyl piperidin-3-ylcarbamate (1.07 g, 5.35 mmol, 1.50 equiv), acetic acid (1.03 g, 17.17 mmol, 6.00 equiv) and NaBH3CN (720 mg, 11.43 mmol, 4.00 equiv). The resulting mixture was stirred at 40° C. in an oil bath for 16 hours. The reaction progress was monitored by TLC (DCM: MeOH=10:1). The reaction was then quenched by the addition of NaHCO3 (50 mL). The mixture was then extracted with dichloromethane (4×50 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered off and concentrated on a rotary evaporator. The residue was purified by a silica gel column chromatography eluted with dichloromethane/methanol (50/1) affording tert-butyl 14(943-(dimethylamino)propyl)-9H-carbazol-3-yl)methyl)piperidin-3-yl carbamate as brown oil (0.5 g).

1. customThe reaction was then quenched by the addition of NaHCO3 (50 mL)
2. extractionThe mixture was then extracted with dichloromethane (4×50 mL)
3. dry with materialCombined organic layers were dried over anhydrous sodium sulfate
4. filtrationfiltered off
5. concentrationconcentrated on a rotary evaporator
6. customThe residue was purified by a silica gel column chromatography
7. washeluted with dichloromethane/methanol (50/1)

ORD record

ord-53c40b56fbb9437b8c71922bdeda1b5b

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08080566B1