Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 178502717, compound

Participants

Role	Name	HCID	Charge
Reactant	Methanamine, N-methoxy-, hydrochloride (1:1)	HCID 81138	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	HCID 178461286	HCID 178461286	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 178502717	HCID 178502717	—

Reaction Steps

To a solution of trans-4-methylcyclohexanecarboxylic acid (100 g, 0.70 mol) in DMF (1.2 L) were added HATU (294 g, 0.77 mol) and DIPEA (273 g, 2.1 mol) at room temperature. After stirring for 0.5 h, TLC showed no starting material left (petroleum ether/ethyl acetate=5:1). Then N,O-dimethylhydroxylamine hydrochloride (75.5 g, 0.77 mol) was added slowly. The mixture was stirred at room temperature for 3 h. TLC (petroleum ether/ethyl acetate=5:1) showed the reaction was complete. The reaction was diluted with water and extracted with ethyl acetate. The organic layer was washed with water twice, washed with brine, dried over Na2SO4 and concentrated to give crude trans-N-methoxy-N,4-dimethylcyclohexanecarboxamide, which was used for the next step without further purification.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08846657B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-5a522d0d66a640d0a808c3282e97618d
Source note	uspto-grants-2014_09