Methyl iodide → Diisopropyl Ether

Participants

Role	Name	HCID	Charge
Reactant	Methyl iodide	HCID 6328	—
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	Sodium hydride	HCID 24758	—
Reactant	Benzamide, N-(1-acetyl-4-piperidinyl)-4-fluoro-	HCID 9816738	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	Diisopropyl Ether	HCID 7914	—
Product	N-(1-acetylpiperidin-4-yl)-N-methyl-4-fluorobenzamide	HCID 9817095	—

Reaction Steps

To a solution of N-(1-acetylpiperidin-4-yl)-4-fluorobenzamide (529 mg) in N,N-dimethylformamide (5 ml) was added sodium hydride (0.1 g). After stirring for 45 minutes, methyl iodide (623 ml) was added to the solution. After stirring for 45 minutes, the mixture was diluted with ethyl acetate (100 ml) and water (50 ml). An organic phase was separated, and washed with water and brine. After drying with magnesium sulfate, the solvents were removed under reduced pressure. After trituration with diisopropyl ether, N-(1-acetylpiperidin-4-yl)-N-methyl-4-fluorobenzamide (248 mg) was obtained.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06710043B1
Source dataset	uspto-grants-2004_03
ORD ID	ord-dfc6e9725237477faeba07e011dfd021
Source note	uspto-grants-2004_03