[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.B(Cl)(Cl)Cl.[CH3:19][S:20][C:21]#N.C(=O)([O-])[O-:24].[Na+].[Na+]>C1(C)C=CC=CC=1.O>[CH3:19][S:20][C:21](=[O:24])[C:10]1[C:9](=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH:8][CH:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1
To a solution of 1.14 g of N-(1-methyl-4-piperidinyl)aniline in 20 ml of toluene was added 3.6 ml of a solution of 2.04M boron trichloride--toluene and the mixture was refluxed with heating on an oil bath for 2 hr. After cooling, the reaction mixture was mixed with 0.49 ml of methyl thiocyanate and refluxed with heating on an oil bath for 2 hr. After cooling, 20 ml of water was added and the mixture was stirred at 110° C. on an oil bath for 1 hr. The rection mixture was turned to basic conditions with aqueous 2N sodium carbonate and extracted with toluene. The toluene layer was dried over anhydrous magnesium sulfate, chromatographed on a column of 20 g of aluminium oxide for purification, eluted with methylene chloride and concentrated. The crystalline residue (1.35 g) was recrystallized from ether--petroleum ether to give 1.21 g of N-(1-methyl-4-piperidinyl)thioanthranilic acid S-methyl ester melting at 64°-65° C. as yellow crystals.
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