Aniline → Benzenamine, N-2-cyclohexen-1-yl-

Hydroamination of 1,3-Dienes with Arylamines: Sixteen examples of hydroamination of 1,3-dienes with arylamines are shown in Table 3 below (Entries 1-16). Typical reaction conditions are 0.5 mmol amine, 2 mmol cyclohexadiene, 2 mol % Pd(PPh3)4, 10 mol % TFA, toluene, 25° C., mixed for 24 hours. A typical procedure is given for Entry 1, Table 1: Pd(PPh3)4 (5.8 mg, 0.0050 mmol) was suspended in 0.1 mL of toluene in a screw-capped vial. 1,3-Cyclohexadiene (160 mg, 190 μL, 2.00 mmol) and aniline (46.6 mg, 45.6 μL, 0.500 mmol) were added to the reaction mixture. The vial was sealed with a cap containing a PTFE septum and removed from the drybox. Trifluoroacetic acid (5.7 mg, 3.9 μL, 0.050 mmol) was added to the reaction mixture by syringe. The reaction mixture was then stirred at room temperature for 24 h. All volatile compounds were evaporated under reduced pressure, and the residue was adsorbed onto silica gel. The product was eluted using 0.5% ethyl acetate/hexanes to give 85.5 mg (99%) of N-cyclohex-2-en-1-ylaniline as a colorless oil. Additional compounds were made in a similar fashion and analyzed as follows.

1. customTypical reaction conditions
2. additionmixed for 24 hours
3. customThe vial was sealed with a cap
4. customremoved from the drybox
5. customAll volatile compounds were evaporated under reduced pressure
6. washThe product was eluted

ORD record

ord-9cf8a6668beb454d806261e7cea3842f

Source dataset

uspto-grants-2002_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06384282B2