Trifluoroacetic acid → HCID 58046573, compound

Participants

Reaction Conditions

Reaction Steps

Trifluoroacetic acid (0.75 ml) was added to a stirred solution of 1-[trans-3-(4-chlorophenyl)allyl]-4-methoxymethylenepiperidine- and 4-tolylhydrazine hydrochloride (28 mg) in chloroform (5 ml) and the reaction was heated to 50° C. for 5 h. Triethylsilane (2 ml) was added and the reaction was heated at 50° C. for a further 5 h. The mixture was allowed to cool and was quenched in concentrated ammonia solution/ice chips (20 ml). The aqueous phase was extracted twice with chloroform and the combined organics were dried over anhydrous magnesium sulphate and concentrated in vacuo to yield 0.04 g (63%) of the desired indoline. 1H NMR (400 MHz, CDCl3) 1.75 (d, J=9 Hz, 2H), 1.96 (td, J=8 & 2, 2H), 2.13 (t, J=9 Hz, 2H), 2.25 (s, 3H), 2.95 (d, J=10 Hz, 2H), 3.19 (d, J=5 Hz, 2H), 3.42 (s, 2H), 6.30 (dt, J=11 & 5 Hz, 1H), 6.48 (d, J=11 Hz, 1H), 6.58 (d, J=7 Hz, 1H), 6.85 (d, J=7 Hz, 1H), 6.9 (s, 1H), 7.30 (m, 4H). MS (ES+) 353/355 (M+H+), 203 (M-4-chlorocinnamyl+H+).

Provenance & Evidence