Acetic Acid → 1-{4-[(Thiophen-3-ylmethyl)amino]phenyl}-butan-1-one

Participants

Reaction Conditions

Reaction Steps

In a 20 mL vial, to a solution of 1-(4-aminophenyl)-butan-1-one (19.64 mg, 0.1 mmol) in DCM/MeOH (0.7 mL) was added a solution of thiophene-3-carbaldehyde (22.4 mg, 0.2 mmol) in DMA (0.8 mL). A solution of acetic acid (18 mg, 0.3 mmol) in DCM/MeOH (0.7 mL) was added, followed by the addition of 160 mg of MP-CNBH3 resin (3 eq.; subst. 2.25 mmoles/g). The vial was capped and was then heated with shaking overnight at 55° C. The progress of the reaction was monitored by LC/MS. After completion of the reaction, the reaction mixture was concentrated to dryness. The residue was dissolved in 1:1 DMSO/MeOH. Purification by reverse phase HPLC (TFA method) gave the title compound.

Provenance & Evidence