4-Nitrobenzaldehyde → HCID 58775945, compound

Participants

Reaction Steps

NaB(OAc)3H (3.5 mmol, 0.75 g) was added to a mixture of 4-nitro-benzaldehyde Compound 4a (2.8 mmol, 0.42 g), (tetrahydro-pyran-4-yl)-methylamine Compound 4b (3.0 mmol, 0.35 g) and glacial acetic acid (3 drops) in CH2Cl2 (50 mL) and the resulting suspension was stirred at r.t. overnight. An aliquot of the reaction mixture showed the formation of product (MS m/e 251; 100%). An aqueous solution of formaldehyde (37% solution, 9.6 mmol, 0.8 mL) was added, followed by NaB(OAc)3H (3.5 mmol, 0.75 g). The reaction mixture was stirred at r.t. for 2 h, then made basic with a 2N NaOH solution and extracted with CH2Cl2. The organic layer was washed with brine, then separated and dried over Na2SO4. The drying agent was filtered and the solvent was removed in vacuo to yield methyl-(4-nitro-benzyl)-(tetrahydro-pyran-4-ylmethyl)-amine Compound 4c as yellow oil (0.63 g, 85% yield). MS m/e 265 (M+H, 100%).

Provenance & Evidence