4-Piperidinol, 1-methyl- → 4-Hydroxy-1-methyl-1-(2-phenoxy-ethyl)-piperidinium bromide

HRID 1690646Notes

Reaction equation

HRID 1690646 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.[O:37]([CH2:44][CH2:45]Br)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[Br-:27].[OH:26][CH:23]1[CH2:24][CH2:25][N+:20]([CH3:19])([CH2:45][CH2:44][O:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:21][CH2:22]1

Participants

5

Reactant 4

HCID 660484-Piperidinol, 1-methyl-HCID 68526Benzene, (2-bromoethoxy)-HCID 133629192-bromo-N-(isoxazol-3-yl)acetamideHCID 87357711(1R/S,3R)-3-Hydroxy-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-piperidinium bromide2×

Product 1

HCID 669022434-Hydroxy-1-methyl-1-(2-phenoxy-ethyl)-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-phenoxy-ethylbromide.

Sources & evidence

ORD record
ord-6e7a44eb210640bbac90ff17a9fad4e9
Source dataset
uspto-grants-2012_04
Patent number
US08153669B2

Reaction notes

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