BIS(4-METHOXYBENZYL)AMINE HCL SALT

Pre aration of Intermediate 1-16.A mixture of p-anisaldehyde (1.8 mL, 14.8 mmol) and 4-methoxybenzylamine (1.9 mL, 14.8 mmol) in EtOH (50 mL) was refluxed for 4 h. On cooling to 0 °C, NaBHPreparation of Intermediate I-16 [0278] [0279] A mixture of p-anisaldehyde (1.8 mL, 14.8 mmol) and 4-methoxybenzylamine (1.9 mL, 14.8 mmol) in EtOH (50 mL) was refluxed for 4 h. On cooling to 0° C., NaBHA solution of 2-(benzylthio)-5-chloropyrazine (0.916 g, 3.87 mmol) in DCM (15 mL, 233 mmol) was treated with water (1.5 mL) and the resultant suspension was cooled to between -5 and o C. Sulfuryl chloride (2.2 mL, 26.2 mmol) was added and the reaction mixture was stirred for 2 hours maintaining the temperature between -5 and o C. A slurry of ice/water (10 mL) was added and the organic phase was collected. The aqueous phase was extracted with DCM (2 x 10 mL) and the combined organic extracts were dried (MgS04) and concentrated in vacuo to afford crude intermediate 5- chloropyrazine-2-sulfonyl chloride as a pale yellow liquid (1.198 g). (1370) A suspension of A solution of benzaldehyde (1.00 g, 9.42 mmol)and benzylamine (1.01 g, 9.42 mmol) in PhMe (120 mL) was heated under reflux inan inert atmosphere with stirring for 16 hours. The H2O generatedwas collected in a Dean-Stark trap. The solvent was removed under vacuum andthe pale yellow oil obtained was dissolved in MeOH (60 mL) before NaBH4(2.1 g, 56.5 mmol) was added. The resulting solution was stirred overnight atroom temperature in an inert atmosphere. The reaction mixture was then treatedwith HCl (2 M, 10 mL), and the solvents were removed under reduced pressure.The solid residue was suspended in NaOH (8 M, 30 mL) and extracted with CHCl3(3 x 60 mL). The combined organic fractions were dried (MgSO4), filtered and the solvents were evaporated off to give I as a pale yellow oil. White crystalline solid (25 %). 1HNMR (300 MHz, CD3CN) d =7.40 (d, 4H), 7.00 (d, 4H), 4.12 (s, 4H), 3.70 (s, 6H).

Molecular Weight:293.79
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:6
Exact Mass:293.1182566
Monoisotopic Mass:293.1182566
Topological Polar Surface Area:30.5
Heavy Atom Count:20
Complexity:207
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes