Triethylamine → 294622-57-4

A solution of ethyl 4-aminopiperidine-1-carboxylate (4.3 g, 0.025 mol) in dry THF was cooled to 0° C. and then treated with triethylamine (3.83 mL, 27.5 mol) and thiophosgene (2.1 mL, 27.5 mmol). The mixture was stirred for 1.5 hours at room temperature, cooled at 0° C. and then treated with ammonium hydroxide solution (7.7 mL, 28% in water). The mixture was stirred for approximately 12 hours and then concentrated by evaporation. The residue was taken up into ethyl acetate and the mixture was treated with a saturated solution of NaHCO3 and brine. The organic phase was separated, dried over sodium sulfate and then concentrated to dryness. The residue was taken up into diethyl ether and a resulting solid was collected by filtration and washed with diethyl ether to provide ethyl 4-thioureidopiperidine-1-carboxylate (4.18 g, 72% V). HNMR (dmso-d6): 7.57 (1H, d), 6.9 (1H, s), 4.05 (1H, bs), 4.02 (2H, q), 3.86 (2H, d), 2.89 (2H, bs), 1.82 (2H, bs), 1.20 (2H, m), 1.17 (3H, t).

1. temperaturecooled at 0° C.
2. stirringThe mixture was stirred for approximately 12 hours
3. concentrationconcentrated by evaporation
4. additionthe mixture was treated with a saturated solution of NaHCO3 and brine
5. customThe organic phase was separated
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated to dryness
8. filtrationa resulting solid was collected by filtration
9. washwashed with diethyl ether

ORD record

ord-d0bbb9cbe1884ffdb4e57c04b282a185

Source dataset

uspto-grants-2002_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06476026B1