Diisopropylamine → N,N-diisopropyl 4-(2-methylphenyl)benzamide

To a suspension of 4-(2-methylphenyl)benzoic acid (4.00 g, 18.8 mmol) in DCM (150 mL) was added oxalyl chloride (10.00 g, 78.8 mmol) followed by 5 drops of DMF. The reaction mixture was stirred at RT for 3 h until a clear solution resulted. The solvent was removed in vacuo. The residue was dissolved with DCM (100 mL) and treated with aq. potassium carbonate (3.41 mL, 56.5 mmol). The reaction mixture was cooled to 0° C., and a solution of diisopropylamine (5.33 mL, 37.7 mmol) in DCM (50 mL) was added dropwise. The resulting mixture was stirred at RT over 12 h. The resulting mixture was quenched by the slow addition of saturated aqueous Na2CO3 (100 mL). The organic phase was separated and aqueous phase was extracted with dichloromethane (3×60 mL). The combined organic phases were washed with brine. The resulting organic solution was then dried over magnesium sulfate and concentrated under reduced pressure to give N,N-diisopropyl 4-(2-methylphenyl)benzamide as an off-white solid. MS (ESI, pos.ion) m/z: 296 (M+1)

1. customresulted
2. customThe solvent was removed in vacuo
3. dissolutionThe residue was dissolved with DCM (100 mL)
4. temperatureThe reaction mixture was cooled to 0° C.
5. stirringThe resulting mixture was stirred at RT over 12 h
6. customThe resulting mixture was quenched by the slow addition of saturated aqueous Na2CO3 (100 mL)
7. customThe organic phase was separated
8. extractionaqueous phase was extracted with dichloromethane (3×60 mL)
9. washThe combined organic phases were washed with brine
10. dry with materialThe resulting organic solution was then dried over magnesium sulfate
11. concentrationconcentrated under reduced pressure

ORD record

ord-d6870ee9b04b480cbedaff09dc6b52a3

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07759337B2