4-Hydroxy-1-methyl-1-(pyrazin-2-ylcarbamoylmethyl)-piperidinium bromide → 4-(2-Cyclohexyl-2-hydroxy-2-phenyl-acetoxy)-1-methyl-1-(pyrazin-2-ylcarbamoylmethyl)-piperidinium bromide

HRID 1690650Notes

Reaction equation

HRID 1690650 reaction equation
[Br-:1].[CH:2]1([C:8]([OH:34])([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:9]([O:11][CH2:12]C2CCC[N+]2(C(C2C=CON=2)C(=O)N)C)=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[Br-].OC[C@H]1CCC[N+]1(CC(=O)NC1C=CON=1)C.[Br-].OC1[CH2:60][CH2:59][N+:58]([CH3:71])([CH2:61][C:62](=[O:70])[NH:63][C:64]2[CH:69]=[N:68][CH:67]=[CH:66][N:65]=2)[CH2:57][CH2:56]1>>[Br-:1].[CH:2]1([C:8]([OH:34])([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:9]([O:11][CH:12]2[CH2:56][CH2:57][N+:58]([CH3:71])([CH2:61][C:62](=[O:70])[NH:63][C:64]3[CH:69]=[N:68][CH:67]=[CH:66][N:65]=3)[CH2:59][CH2:60]2)=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 866342214-Hydroxy-1-methyl-1-(pyrazin-2-ylcarbamoylmethyl)-piperidinium bromide2×HCID 131729615(1R/S,2R)-2-Hydroxymethyl-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-pyrrolidinium bromideHCID 131729617(R/S)-(2-Cyclohexyl-2-hydroxy-2-phenyl-acetoxymethyl)-1-(isoxazol-3-yl carbamoylmethyl)-1-methyl-pyrrolidinium bromide

Product 1

HCID 871978944-(2-Cyclohexyl-2-hydroxy-2-phenyl-acetoxy)-1-methyl-1-(pyrazin-2-ylcarbamoylmethyl)-piperidinium bromide

Procedure

This compound is prepared by an analogous method to (1R/S,2R)-2-((R/S)-(2-Cyclohexyl-2-hydroxy-2-phenyl-acetoxymethyl)-1-(isoxazol-3-yl carbamoylmethyl)-1-methyl-pyrrolidinium bromide (Example 1) by replacing (1R/S,2R)-2-hydroxymethyl-1-(isoxazol-3-ylcarbamoyl-methyl)-1-methyl-pyrrolidinium bromide (Intermediate B) with 4-hydroxy-1-methyl-1-(pyrazin-2-ylcarbamoylmethyl)-piperidinium bromide (Intermediate H).

Sources & evidence

ORD record
ord-ffff1a0573f547d0b8f58b8a77c06dd4
Source dataset
uspto-grants-2012_04
Patent number
US08153669B2

Reaction notes

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