Maleic Acid → [1-[2-[(Methylsulphonyl)methylamino]ethyl]4-piperidinyl]methyl[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]carbamate (Z)-2-butenedioate

HRID 53248Notes

Reaction equation

HRID 53248 reaction equation
[CH3:1][S:2]([CH2:5][NH:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16](=[O:31])[N:17]([CH3:30])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]2[O:28][N:27]=[C:26]([CH3:29])[N:25]=2)[CH2:11][CH2:10]1)(=[O:4])=[O:3].[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]\[C:35]([OH:37])=[O:36]>C(OCC)(=O)C>[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]\[C:35]([OH:37])=[O:36].[CH3:1][S:2]([CH2:5][NH:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16](=[O:31])[N:17]([CH3:30])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]2[O:28][N:27]=[C:26]([CH3:29])[N:25]=2)[CH2:11][CH2:10]1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 86750684HCID 86750684, compound

Product 1

HCID 86750683[1-[2-[(Methylsulphonyl)methylamino]ethyl]4-piperidinyl]methyl[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]carbamate (Z)-2-butenedioateYield 73.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

[1-[2-[(Methylsulphonyl)methylamino]ethyl]-4-piperidinyl]methyl[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]carbamate (55 mg) was dissolved in boiling ethyl acetate (1 ml) and maleic acid (17 mg) in hot ethyl acetate (1 ml) added. White crystals precipitated. These were filtered and dried under vacuum to give the title compound (51 mg), as a white powder, m.p. 170°-172°

Workup

  1. additionadded
  2. customWhite crystals precipitated
  3. filtrationThese were filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-a175068cb1484a3e8e9a7acf931dcddd
Source dataset
uspto-grants-1997_04
Patent number
US05618827

Reaction notes

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