Hydrochloric Acid → N-(3,4-dichlorophenyl)-1-[(3R)-piperidin-3-ylmethyl]piperidine-4-carboxamide

HRID 603237Notes

Reaction equation

HRID 603237 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl>CO.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([CH:12]2[CH2:13][CH2:14][N:15]([CH2:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]3)[CH2:16][CH2:17]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57656896tert-butyl (3S)-3-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperidin-1-yl)methyl]piperidine-1-carboxylate

Product 1

HCID 57656947N-(3,4-dichlorophenyl)-1-[(3R)-piperidin-3-ylmethyl]piperidine-4-carboxamideYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl (3S)-3-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperidin-1-yl)methyl]piperidine-1-carboxylate (2.3 g) in methanol (50 mL) was added 4M HCl in dioxane (15 mL). The mixture was stirred at room temperature for 18 hours and then evaporated. The residue was then partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate. The layers were separated and the organic extract was evaporated. The residue was triturated with dichloromethane and filtered to give the title compound as a white solid (1.5 g, 83%)

Workup

  1. customevaporated
  2. customThe residue was then partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate
  3. customThe layers were separated
  4. extractionthe organic extract
  5. customwas evaporated
  6. customThe residue was triturated with dichloromethane
  7. filtrationfiltered

Sources & evidence

ORD record
ord-11eeb7b365c0484b9e8d78179b95e914
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

Loading…