m-Tolyl isocyanate → HCID 20097184, compound
Reaction equation
[NH2:1][CH2:2][C:3]([N:5]([CH2:12][C:13]([N:15]1[CH2:20][CH:19]([CH2:21][CH3:22])[CH2:18][CH2:17][CH:16]1[CH3:23])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[CH3:24][C:25]1[CH:26]=[C:27]([N:31]=[C:32]=[O:33])[CH:28]=[CH:29][CH:30]=1>>[CH2:21]([CH:19]1[CH2:20][N:15]([C:13](=[O:14])[CH2:12][N:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3](=[O:4])[CH2:2][NH:1][C:32]([NH:31][C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([CH3:24])[CH:26]=2)=[O:33])[CH:16]([CH3:23])[CH2:17][CH2:18]1)[CH3:22]Participants
Procedure
The procedure is analogous to that described in Example 1, but 2.0 g of 2-amino-N-[2-(5-ethyl-2-methylpiperidino)-2-oxoethyl]-N-phenylacetamide, as a mixture of the cis and trans isomers, and 0.8 g of 3-methylphenyl isocyanate are used as the starting material. The crude product obtained is purified by chromatography on 50 g of silica (0.065-0.200 mm) contained in a column 1.5 cm in diameter [eluent: methylene chloride/methanol (98-2 by volume)], collecting 20 cm3 fractions. Fractions 2 to 8 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization from an ethyl acetate/diethyl ether mixture (40-60 by volume), 0.5 g of N-[2-(5-ethyl-2-methylpiperidino)-2-oxoethyl]-2-[3-(3-methylphenyl)ureido]-N-phenylacetamide is obtained as a mixture of the cis and trans isomers melting at 158° C.
Workup
- customThe crude product obtained
- customis purified by chromatography on 50 g of silica (0.065-0.200 mm)
- customcollecting 20 cm3 fractions
- concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
- customAfter recrystallization from an ethyl acetate/diethyl ether mixture (40-60 by volume)
Sources & evidence
- ORD record
- ord-73e31601b59a4fd1ba63f6281dab1b63
- Source dataset
- uspto-grants-1995_01
- Patent number
- US05382590
Reaction notes
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