6-Benzenesulfonyl-naphthalene-1-carbonitrile → C-(6-Benzenesulfonyl-naphthalen-1-yl)-methylamine

Participants

Reaction Steps

6-Benzenesulfonyl-naphthalene-1-carbonitrile is dissolved in dry THF and cooled to ice bath temperature. Borane-THF complex is added and the reaction mixture is stirred under nitrogen overnight at room temperature. The reaction is quenched by addition of HCl and methanol, and made basic by addition of 1M NaOH. The resulting residue is extracted with EtOAc, and the organic layer is dried (MgSO4), filtered and concentrated under reduced pressure. The residue is recrystallized from HCl/EtOH to give C-(6-Benzenesulfonyl-naphthalen-1-yl)-methylamine as a hydrochloride salt.

Provenance & Evidence