m-Tolyl isocyanate → HCID 14996863, compound

HRID 1769693Notes

Reaction equation

HRID 1769693 reaction equation
[NH2:1][CH2:2][C:3]([N:5]([CH2:12][C:13]([N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[CH3:21])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[CH3:22][C:23]1[CH:24]=[C:25]([N:29]=[C:30]=[O:31])[CH:26]=[CH:27][CH:28]=1>>[CH3:21][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][N:15]1[C:13](=[O:14])[CH2:12][N:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3](=[O:4])[CH2:2][NH:1][C:30]([NH:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([CH3:22])[CH:24]=1)=[O:31]

Participants

3

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 14996862HCID 14996862, compound

Product 1

HCID 14996863HCID 14996863, compoundYield 37.8%

Procedure

The procedure is analogous to that described in Example 1, but 1.45 g of (RS)-2-amino-N-[2-(2-methylpiperidino)-2-oxoethyl]-N-phenylacetamide and 0.67 g of 3-methylphenyl isocyanate used as the starting material. After recrystallization from a mixture of ethanol and diisopropyl ether (50-50 by volume), 0.80 g of (RS)-N-[2-(2-methylpiperidino)-2-oxoethyl]-2-[3-(3-methylphenyl)ureido]-N-phenylacetamide melting at 188° C. is obtained.

Workup

  1. customAfter recrystallization
  2. additionfrom a mixture of ethanol and diisopropyl ether (50-50 by volume)

Sources & evidence

ORD record
ord-aa95a29a21b746cea9037e566fdc00b8
Source dataset
uspto-grants-1995_01
Patent number
US05382590

Reaction notes

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