Benzeneacetamide, 4-chloro-alpha-(4-chlorophenyl)- → 2,2-Bis(4-chlorophenyl)ethanamine

To a solution of 2,2-bis-(4-chloro-phenyl)-acetamide (0.50 g, 1.8 mmol) in THF (10 mL) at rt was added BH3-THF (1.0 M in THF, 4.5 mL, 4.5 mmol). The solution was heated at reflux for 2 h. The mixture was cooled in an ice bath, and the excess BH3 was quenched by careful addition of 10 mL of MeOH. HCl (2.0 M in MeOH, 5 mL) was added, and the resulting mixture was heated at reflux for 1 h. After cooling, the mixture was concentrated, and the residue was partitioned between 1 N HCl and Et2O. The acidic aqueous layer was basified with 10 N NaOH and extracted with Et2O (3×). The combined organic extracts were dried (MgSO4) and concentrated to provide the desired amine (181 mg, 38%). The amine was used without further purification. 1H NMR (400 MHz, CDCl3): 7.30-7.26 (m, 4H), 7.18-7.12 (m, 4H), 3.94 (t, J=7.5, 1H), 3.28 (d, J=7.6, 2H), 1.06 (br s, 2H).

1. temperatureThe solution was heated
2. temperatureat reflux for 2 h
3. temperatureThe mixture was cooled in an ice bath
4. customthe excess BH3 was quenched by careful addition of 10 mL of MeOH
5. additionHCl (2.0 M in MeOH, 5 mL) was added
6. temperaturethe resulting mixture was heated
7. temperatureat reflux for 1 h
8. temperatureAfter cooling
9. concentrationthe mixture was concentrated
10. customthe residue was partitioned between 1 N HCl and Et2O
11. extractionextracted with Et2O (3×)
12. dry with materialThe combined organic extracts were dried (MgSO4)
13. concentrationconcentrated

ORD record

ord-37606b358a074a83aa1583fb6e3ebf65

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07855292B2