1,4-Dioxane hydrochloride → 1-{2-[(6-Aminohexanoyl)(methyl)amino]ethyl}piperidin-4-yl biphenyl-2-ylcarbamate dihydrochloride

HRID 446511Notes

Reaction equation

HRID 446511 reaction equation
[C:1]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:35])[O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]([C:20](=[O:34])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26]C(OC(C)(C)C)=O)[CH3:19])[CH2:12][CH2:11]1.[ClH:42].O1CCOCC1>O1CCOCC1>[ClH:42].[ClH:42].[C:1]1([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:35])[O:9][CH:10]1[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][N:18]([C:20](=[O:34])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])[CH3:19])[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 666716851-{2-[{6-[(tert-Butoxycarbonyl)amino]hexanoyl}(methyl)amino]ethyl}piperidin-4-yl biphenyl-2-ylcarbamate

Product 1

HCID 666717251-{2-[(6-Aminohexanoyl)(methyl)amino]ethyl}piperidin-4-yl biphenyl-2-ylcarbamate dihydrochlorideYield 105.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The compound (1.59 g, 2.80 mmol) obtained in Example 11b was dissolved in 1,4-dioxane (7 mL), 4 N hydrochloric acid-dioxane (7.00 mL, 28.0 mmol) was added under ice cooling, and the mixture was stirred at room temperature for 20 minutes. Since insoluble material was precipitated, methanol (4 mL) was added, and the mixture was stirred at room temperature for 40 minutes. The solvent was evaporated under reduced pressure to give the title compound (1.60 g; yield, 100%) as a white solid.

Workup

  1. customSince insoluble material was precipitated
  2. additionmethanol (4 mL) was added
  3. stirringthe mixture was stirred at room temperature for 40 minutes
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9cd9c3d50dab49938357f0c0383896cc
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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