4-Piperidinol, 1-methyl- → 4-Hydroxy-1-methyl-1-(pyrazin-2-ylcarbamoylmethyl)-piperidinium bromide

HRID 1690642Notes

Reaction equation

HRID 1690642 reaction equation
[Br-].O[C@@H]1CCC[N+](CC(=O)NC2C=CON=2)(C)C1.[CH3:19][N:20]1[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]1.[Br:27]CC(NC1C=CON=1)=O.Br[CH2:38][C:39]([NH:41][C:42]1[CH:47]=[N:46][CH:45]=[CH:44][N:43]=1)=[O:40]>>[Br-:27].[OH:26][CH:23]1[CH2:24][CH2:25][N+:20]([CH3:19])([CH2:38][C:39](=[O:40])[NH:41][C:42]2[CH:47]=[N:46][CH:45]=[CH:44][N:43]=2)[CH2:21][CH2:22]1

Participants

5

Reactant 4

HCID 660484-Piperidinol, 1-methyl-HCID 133629192-bromo-N-(isoxazol-3-yl)acetamideHCID 445426692-bromo-N-(pyrazin-2-yl)acetamide2×HCID 87357711(1R/S,3R)-3-Hydroxy-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-piperidinium bromide2×

Product 1

HCID 866342214-Hydroxy-1-methyl-1-(pyrazin-2-ylcarbamoylmethyl)-piperidinium bromide

Procedure

This compound is prepared by an analogous method to (1R/S,3R)-3-Hydroxy-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-piperidinium bromide (Intermediate C) by replacing (R)-1-methyl-piperidin-3-ol (step C3) with 1-methyl-piperidin-4-ol and by replacing 2-bromo-N-isoxazol-3-yl-acetamide (Intermediate A) with 2-bromo-N-pyrazin-2-yl-acetamide (Intermediate G).

Sources & evidence

ORD record
ord-5bea74143eba4caaa7e632ccb78cfaa3
Source dataset
uspto-grants-2012_04
Patent number
US08153669B2

Reaction notes

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