Triethylamine → HCID 18337220, compound

Commercially available tert-butyl 4-aminopiperidine-1-carboxylate (0.50 g, 1.0 eq) was taken up in dichloromethane and treated with triethylamine (0.42 mL, 1.2 eq). After stirring for 5 minutes, thiophene-2-carbonyl chloride (0.29 ml, 1.1 eq) was slowly added. The reaction stiffed for 15 hours at room temperature. To work up, dichloromethane (5 mL) was added. The organics were washed with water (3×-5 mL) then dried over Na2SO4 and concentrated for 0.80 g tan oil (obs M+Na 323, calc M+Na 323). This product was dissolved in dioxane (5 mL) and treated with 4 N HCl in dioxane (1.88 ml). After stiffing for 15 hours at room temperature, the reaction was concentrated to oily residue (0.63 g, 100% over 2 steps, calc M+H 211, obs M+H 211).

1. waitThe reaction stiffed for 15 hours at room temperature
2. washThe organics were washed with water (3×-5 mL)
3. dry with materialthen dried over Na2SO4
4. concentrationconcentrated for 0.80 g tan oil (obs M+Na 323, calc M+Na 323)
5. dissolutionThis product was dissolved in dioxane (5 mL)
6. additiontreated with 4 N HCl in dioxane (1.88 ml)
7. waitAfter stiffing for 15 hours at room temperature
8. concentrationthe reaction was concentrated to oily residue (0.63 g, 100% over 2 steps, calc M+H 211, obs M+H 211)

ORD record

ord-5d5c08d7acc74fefa320ee8bebb2b315

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09050334B2