Ammonium Hydroxide → 4-{[2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl]amino}-[(2,6-dimethylphenyl)aminocarbonylmethyl]piperidine

HRID 615384Notes

Reaction equation

HRID 615384 reaction equation
Cl.Cl.[O:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH2:5][CH:4]1[CH:13]([OH:34])[CH2:14][NH:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]([NH:25][C:26]2[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:33])=[O:24])[CH2:18][CH2:17]1.[OH-].[NH4+]>O>[O:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH2:5][CH:4]1[CH:13]([OH:34])[CH2:14][NH:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]([NH:25][C:26]2[C:27]([CH3:33])=[CH:28][CH:29]=[CH:30][C:31]=2[CH3:32])=[O:24])[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 204276944-{[2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl]amino}-1-[(2,6-dimethylphenyl)aminocarbonylmethyl]piperidine dihydrochloride salt

Product 1

HCID 133933564-{[2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl]amino}-[(2,6-dimethylphenyl)aminocarbonylmethyl]piperidineYield 99.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3.5 g of 4-{[2-(1,4-benzodioxan-2-yl)-2-hydroxyethyl]amino}-1-[(2,6-dimethylphenyl)aminocarbonylmethyl]piperidine dihydrochloride salt in water (50 ml) is adjusted to pH 12 with ammonium hydroxide solution and extracted with methylene chloride. The methylene chloride is evaporated to afford 3 g of 4-{[2-(1,4-benzodioxan-2-yl)-2-hydroxyethyl]amino}-[(2,6-dimethylphenyl)aminocarbonylmethyl]piperidine as the free base.

Workup

  1. extractionextracted with methylene chloride
  2. customThe methylene chloride is evaporated

Sources & evidence

ORD record
ord-40e1e07164244f65b17bd5c44feb8c04
Source dataset
uspto-grants-1985_02
Patent number
US04499100

Reaction notes

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