Cyclohexane → HCID 18448416, compound

To a solution of 2,4′-dimethyl-1,1′-biphenyl-3-ylamine (20 g, 0.1015 mol) in anhydrous CH2Cl2 (250 ml) at 0° C. under nitrogen was added triethylamine (28.29 ml, 0.203 mol). Butyrylchloride (11.07 ml, 0.1066 mol) was added dropwise over 0.5 h, the rate of addition ensured temperature of reaction mixture was below 10° C. Reaction mixture was then stirred at room temperature for 2 h under nitrogen, diluted with CH2Cl2 (200 ml), washed with water (400 ml), saturated sodium bicarbonate (400 ml) and saturated sodium chloride (400 ml). The organic solution was dried (Na2SO4) and the solvent removed in vacuo to give a cream solid. To the solid was added cyclohexane (400 ml), the mixture stirred for 2 h and filtered. The solid residues were dissolved in CH2Cl2 and the solvents removed in vacuo to afford the title compound as a cream solid (25 g).

1. additionthe rate of addition
2. customtemperature of reaction mixture
3. customwas below 10° C
4. customReaction mixture
5. washwashed with water (400 ml), saturated sodium bicarbonate (400 ml) and saturated sodium chloride (400 ml)
6. dry with materialThe organic solution was dried (Na2SO4)
7. customthe solvent removed in vacuo
8. customto give a cream solid
9. stirringthe mixture stirred for 2 h
10. filtrationfiltered
11. dissolutionThe solid residues were dissolved in CH2Cl2
12. customthe solvents removed in vacuo

ORD record

ord-b7862f713e404ef7ba977b5b57d51ee8

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07199239B2