Benzylamine → HCID 4730723, compound

Oxalyl chloride (132 μL, 1.5 mmol) was added over a 10 minute period to a mixture of 3-phenylbenzoic acid (200 mg, 1 mmol) dissolved in a mixture THF/DMF (3.5 mL/58 μL). After the addition, the reaction was stirred at room temperature for 2.5 hours. Benzylamine (268 μL, 2.5 mmol) was then added into half of the acid chloride solution at 0° C. The reaction mixture was then stirred at room temperature for 18 hours. The reaction mixture was concentrated and water was added to the residue. The aqueous phase was extracted 3 times with CH2Cl2 and the combined organic layers were washed with 2N HCl, saturated NaHCO3, brine, dried over Na2SO4 and concentrated. Diethyl ether was added to the residue and a white solid precipitated which was collected by filtration and rinsed with a small amount of diethyl ether. The white solid was then dried under vacuum (105 mg, 73%). NMR 1H (ppm, CDCl3): 8.01 (s, 1H), 7.72 (t, J3=7.89 Hz, 2H), 7.58 (d, J3=7.14 Hz, 2H), 7.49-7.24 (m, 9H), 6.57 (br. s., 1H), 4.64 (d, J3=5.29 Hz, 2H).

1. additionAfter the addition
2. stirringThe reaction mixture was then stirred at room temperature for 18 hours
3. concentrationThe reaction mixture was concentrated
4. additionwater was added to the residue
5. extractionThe aqueous phase was extracted 3 times with CH2Cl2
6. washthe combined organic layers were washed with 2N HCl, saturated NaHCO3, brine
7. dry with materialdried over Na2SO4
8. concentrationconcentrated
9. additionDiethyl ether was added to the residue
10. customa white solid precipitated which
11. filtrationwas collected by filtration
12. washrinsed with a small amount of diethyl ether
13. customThe white solid was then dried under vacuum (105 mg, 73%)

ORD record

ord-3a70302248f541508d6278f056cbe016

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07956216B2