Toluene → HCID 10130194, compound

Participants

Reaction Conditions

Reaction Steps

This example is representative of procedure "B". Into a screw-capped test tube were weighed 29 mg (0.052 mmol) Pd(dba)2, 55 mg (0.10 mmol) DPPF, and 144 mg (1.5 mmol) NaO-t-Bu. The solid materials were suspended in 12 ml of toluene. 4-Methylphenyltriflate (240 mg, 1.0 mmol) was dissolved in 1 ml of toluene and added to the test tube. The test tube was sealed with a cap containing a PTFE septum and removed from the dry box. Piperidine (148 μl, 1.5 mmol) was added to the test tube by syringe. The reaction mixture was heated at 100° C. for 5 hours. TLC of the reaction mixture indicated complete consumption of the starting triflate. The reaction mixture was cooled to room temperature, and the mixture was absorbed onto silica gel. Chromatography on a silica gel column using 50:1 hexanes:diethyl ether afforded 1-(4-methylphenyl)piperidine as a clear oil. (135 mg, 77% yield).

Provenance & Evidence