Water → 4-[(4-Methoxy-2-methylphenyl)amino]butanenitrile

Temperature

110 °C

A solution of DIPEA (39 mL, 1 eq) and 4-methoxy-2-methylaniline (30 g, 0.22 mol) in anh. DMF (90 mL), under N2, was heated at 100° C. 4-Bromobutanenitrile (21 mL, 1 eq) was added dropwise. The internal temperature was raised to 110° C. and the reaction mixture was stirred for 2 hr. The mixture was cooled down to r.t. and diluted with MTBE (240 mL). Water (270 mL) was added and the phases were separated. The organic layer was further washed with water (150 mL) and evaporated to 150 mL. Fresh MTBE (150 mL) was added and the mixture again evaporated to 150 mL. The mixture was treated with cHex (540 mL) over 20 min and the resulting suspension left at room temperature for 1.5 hr. The suspension was filtered and the cake washed with a mixture MTBE (30 mL)/cHex (90 mL). The title compound was collected as a violet solid (23.8 g, 53%).

1. temperatureThe mixture was cooled down to r.t.
2. customthe phases were separated
3. washThe organic layer was further washed with water (150 mL)
4. customevaporated to 150 mL
5. additionFresh MTBE (150 mL) was added
6. customthe mixture again evaporated to 150 mL
7. additionThe mixture was treated with cHex (540 mL) over 20 min
8. waitthe resulting suspension left at room temperature for 1.5 hr
9. filtrationThe suspension was filtered
10. washthe cake washed with a mixture MTBE (30 mL)/cHex (90 mL)
11. customThe title compound was collected as a violet solid (23.8 g, 53%)

ORD record

ord-d05173fab68a4c6fb523290b44ef5141

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07427630B2