Water → 4-(2-Hydroxy-2,2-diphenyl-acetoxy)-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-piperidinium bromide

HRID 1690656Notes

Reaction equation

HRID 1690656 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9](=[O:24])[C:10]([OH:23])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:4][CH2:3]1.[Br:25][CH2:26][C:27]([NH:29][C:30]1[CH:34]=[CH:33][O:32][N:31]=1)=[O:28].O>C(#N)C>[Br-:25].[OH:23][C:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:9]([O:8][CH:5]1[CH2:6][CH2:7][N+:2]([CH2:26][C:27](=[O:28])[NH:29][C:30]2[CH:34]=[CH:33][O:32][N:31]=2)([CH3:1])[CH2:3][CH2:4]1)=[O:24]

Participants

5

Reactant 3

HCID 962WaterHCID 771571-Methyl-4-piperidyl benzilate2×HCID 133629192-bromo-N-(isoxazol-3-yl)acetamide2×

Product 1

HCID 866342234-(2-Hydroxy-2,2-diphenyl-acetoxy)-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-piperidinium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution comprising hydroxy-diphenyl-acetic acid 1-methyl-piperidin-4-yl ester (Intermediate F) (0.25 g, 0.77 mmol) in acetonitrile (5 ml) under an inert atmosphere of argon is added 2-bromo-N-isoxazol-3-yl-acetamide (Intermediate A). The reaction mixture is stirred overnight at room temperature and then water is added. Acetonitrile is removed in vacuo and the resulting mixture is decanted into a clean flask and left overnight. The solid that formed is filtered to yield the titled product.

Workup

  1. customAcetonitrile is removed in vacuo
  2. customthe resulting mixture is decanted into a clean flask
  3. waitleft overnight
  4. customThe solid that formed
  5. filtrationis filtered

Sources & evidence

ORD record
ord-748fbcb4ea6e446690f21f26828ba114
Source dataset
uspto-grants-2012_04
Patent number
US08153669B2

Reaction notes

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