Diethyl Ether → Piperidine-1-carboximidamide Hydrochloride

A mixture of piperidine (4.95 ml, 50 mmol), diisopropylethylamine (8.73 ml, 50.0 mmol) and 1H-1,2,4-triazole-1-carboximidamide hydrochloride (6.11 g, 55.0 mmol) in N,N-dimethylformamide (20 ml) was stirred at room temperature over the weekend. Ether (50 ml) was added to the reaction mixture and the mixture was stirred at room temperature for 10 minutes. The ether layer was separated and DMF layer was stirred with ether (50 ml) at 5° C. (ice water bath) for 10 minutes and the ether layer was separated from the residue. Ether (30 ml) was added to the residue and the mixture was stirred at 5° C. The resulting solid was triturated with ether, collected, washed with ether and dried to give the title compound as a colourless solid (3.55 g, 43%). LC/MS [M+H]+=128.

1. stirringthe mixture was stirred at room temperature for 10 minutes
2. customThe ether layer was separated
3. stirringDMF layer was stirred with ether (50 ml) at 5° C. (ice water bath) for 10 minutes
4. customthe ether layer was separated from the residue
5. additionEther (30 ml) was added to the residue
6. stirringthe mixture was stirred at 5° C
7. customThe resulting solid was triturated with ether
8. customcollected
9. washwashed with ether
10. customdried

ORD record

ord-a4b2591ad76044a69c5ccfd211b45762

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133178B2