2,4,6-Trichloroaniline → 2,4,6-Trichloro-N-methylaniline
Reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]([Cl:10])[C:3]=1[NH2:4].[CH2:11](N1[C@H](C)CN([C@H](C2C=C(C=CC=2)C(Cl)=O)C2C=CC=C(O[Si](C(C)(C)C)(C)C)C=2)[C@@H](C)C1)C=C>>[CH3:11][NH:4][C:3]1[C:2]([Cl:1])=[CH:8][C:7]([Cl:9])=[CH:6][C:5]=1[Cl:10]Participants
3
Procedure
N-Methyl-2,4,6-trichloroaniline [NMR (200 MHz, CDCl3): δ 2.82 (s, 3H); 5.11 (s, 1H); 7.46 (s, 2H)] was prepared from 2,4,6-trichloroaniline, coupled with 3-((αR)-α-((2S, 5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-(tert-butyldimethylsilyloxy)benzyl)benzoyl chloride, deprotected and purified by the methods described in Example 10 to give (+)-3-((αR)-α-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N-methyl-N-(2,4,6-trichlorophenyl) as an off-white powder.
Workup
- custom