N-methyl-2-pyrrolidone → HCID 67163590, compound

Participants

Role	Name	HCID	Charge
Reactant	N-methyl-2-pyrrolidone	HCID 13387	—
Reactant	4-Bromo-2-chlorobenzenesulfonyl chloride	HCID 2734766	—
Reactant	Aluminium lithium hydride	HCID 21226445	—
Reactant	4-Aminomethyl-N-tert-butyl-3-methyl-benzenesulfonamide	HCID 58275344	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	HCID 67163590	HCID 67163590	—

Reaction Conditions

Temperature	150 °C

Reaction Steps

4-Aminomethyl-N-tert-butyl-2-chloro-benzenesulfonamide was synthesized in a manner analogous to 4-Aminomethyl-N-tert-butyl-3-methyl-benzenesulfonamide in Example 4, using 4-bromo-2-chlorobenzene-1-sulfonyl chloride in place of 4-bromo-3-methylbenzene-1-sulfonyl chloride. In the second step NMP was used as the solvent, Pd(dppf)Cl2 alone was used as catalyst and the reaction mixture was stirred at 150° C. for 30 min, then heated at 120° C. overnight. Reduction of the cyano group to aminomethyl group in the last step was achieved by stirring with lithium aluminium hydride from 0° C. to room temperature in THF.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08536187B2
Source dataset	uspto-grants-2013_09
ORD ID	ord-f69782123a1947439e1ac794e0519fd0
Source note	uspto-grants-2013_09