4-Nitrobenzaldehyde → 1-Methyl-4-(4-nitrobenzyl)piperazine

To a 0° C. cooled solution of 4-nitrobenzaldehyde in DCM (40 mL) was added Na(OAc)3BH (10.526 gm, 49.66 mmol) and the reacton was stirred for 10 min. To the reaction mixture was added N-methylpiperazine (9.93 g, 99.3 mmol) under nitrogen atmosphere and the reaction mixture was continued stirring at room temperature for 4 h. The progress of the reaction was monitored by TLC and upon completion of the reaction, the mixture was partitioned between DCM (20 mL) and water (15 mL) and the organic layer was separated, washed with water (2×15 mL), dried over sodium sulphate, filtered and the solvent was removed under reduced pressure to give crude residue. Washing with ether gave 1-methyl-4-(4-nitrobenzyl)piperazine (4 g). 1H NMR (CDCl3, 200 MHz) δ: 8.19 (2H, d, J=8.4 Hz), 7.53 (2H, d, J=8.4 Hz), 3.59 (2H, s), 2.47 (8H, bm), 2.29 (3H, s); m/e=236 (M+1).

1. stirringthe reaction mixture was continued stirring at room temperature for 4 h
2. customThe progress of the reaction was monitored by TLC and upon completion of the reaction
3. customthe mixture was partitioned between DCM (20 mL) and water (15 mL)
4. customthe organic layer was separated
5. washwashed with water (2×15 mL)
6. dry with materialdried over sodium sulphate
7. filtrationfiltered
8. customthe solvent was removed under reduced pressure
9. customto give crude residue
10. washWashing with ether

ORD record

ord-f09d761aca3640698a4ac7c12f7da2a3

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07772245B2