1,4-Dioxane hydrochloride → N,N-dibenzylpiperidine-4-carboxamide

HRID 1743816Notes

Reaction equation

HRID 1743816 reaction equation
[CH2:1]([N:8]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:9]([CH:11]1[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCOCC1.Cl>CO>[CH2:24]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]([CH:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1)=[O:10])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 22236495Tert-butyl 4-[(dibenzylamino)carbonyl]piperidine-1-carboxylate

Product 1

HCID 22236499N,N-dibenzylpiperidine-4-carboxamideYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of tert-butyl 4-[(dibenzylamino)carbonyl]piperidine-1-carboxylate (EXAMPLE 4, Step 1, 4.0 g, 10.0 mmol) in methanol (550 mL) was added 4N HCl dioxane solution (80 mL, 320 mmol) at 0° C. The mixture was stirred for 6 h and evaporated. The resulting amorphous was dissolved in aqueous ammonia and the mixture was extracted with dichloromethane. The combined extract was dried over magnesium sulfate, and concentrated to afford 3.0 g (99%) of the title compound as a colorless amorphous powder.

Workup

  1. customevaporated
  2. dissolutionThe resulting amorphous was dissolved in aqueous ammonia
  3. extractionthe mixture was extracted with dichloromethane
  4. extractionThe combined extract
  5. dry with materialwas dried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8b4e349b459b4bc1a86c9757865e9ad7
Source dataset
uspto-grants-2006_03
Patent number
US07012080B2

Reaction notes

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