Hydrochloric Acid → Benzenemethanamine, 3,5-dichloro-N-methyl-, hydrochloride

To a stirred solution of 3,5-dichlorobenzaldehyde (9.0 g, 51 mmol) in methanol (100 mL) was added methanolic methylamine (2M, 100 mL, 200 mmol) and the resulting mixture stirred for 2 h at room temperature. To this was added a solution of ZnCl2 (3.402 g, 25 mmol) slowly and NaCNBH3 (3.142 g, 50 mmol) in methanol (100 mL). After 24 h, the reaction mixture was concentrated, and the resulting residue taken up in dilute aq NaOH (0.5 N, 200 mL) and extracted with CH2Cl2 (5×50 mL). The combined CH2Cl2 extracts were dried over anhydrous Na2SO4, filtered and concentrated to give a yellow viscous liquid. The crude product was dissolved in ether (200 mL) to which was added 29 mL of 2N HCl (in ether). The resulting white 3,5-dichlorobenzyl-methylamine hydrochloride salt was filtered and dried under vacuum to give 11.20 g (97% yield) of product. 1HNMR (300 MHz, DMSO-d6) δ: 9.48 (2H, s), 7.68 (3H, s), 4.13 (2H, s), 2.50 (3H, s). MS calcd for C8H10C12N (M+H): 190.02. found: 190.05.

1. waitAfter 24 h
2. concentrationthe reaction mixture was concentrated
3. extractionextracted with CH2Cl2 (5×50 mL)
4. dry with materialThe combined CH2Cl2 extracts were dried over anhydrous Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customto give a yellow viscous liquid
8. filtrationThe resulting white 3,5-dichlorobenzyl-methylamine hydrochloride salt was filtered
9. customdried under vacuum

ORD record

ord-45e53a0ec6744d269ae6ddfce2eb3329

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07109186B2