Ethyl Acetate → [1-(1-Methylethyl)-4-piperidinyl]methyl[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]carbamate Maleate

HRID 53249Notes

Reaction equation

HRID 53249 reaction equation
[CH3:1][CH:2]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11](=[O:26])[N:12]([CH3:25])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[O:23][N:22]=[C:21]([CH3:24])[N:20]=2)[CH2:6][CH2:5]1)[CH3:3].C(OCC)(=O)C.[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37]>CO>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37].[CH3:3][CH:2]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11](=[O:26])[N:12]([CH3:25])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[O:23][N:22]=[C:21]([CH3:24])[N:20]=2)[CH2:6][CH2:5]1)[CH3:1]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 444266Maleic AcidHCID 86750686HCID 86750686, compound

Product 1

HCID 86750685[1-(1-Methylethyl)-4-piperidinyl]methyl[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]carbamate MaleateYield 70.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a warm solution of [1-(1-methylethyl)-4-piperidinyl]methyl[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]carbamate (120 mg) in the minimum amount of ethyl acetate was added a solution of maleic acid (36.9 mg) in the minimum amount of warm methanol (2 ml). Concentration in vacuo left a white oily residue which was triturated twice in ether (10 ml). The resulting white powder was filtered and dried in vacuo to yield the title compound as a light brown solid (107 mg), m.p. 89°-93°.

Workup

  1. concentrationConcentration in vacuo
  2. waitleft a white oily residue which
  3. customwas triturated twice in ether (10 ml)
  4. filtrationThe resulting white powder was filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-cbfb8729a3bc43b0ab070af20e78601b
Source dataset
uspto-grants-1997_04
Patent number
US05618827

Reaction notes

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