2,3-Dihydroxybutanedioic Acid → 3-[4-(2-Pyridyl)piperidin-1-yl]propylamine l-tartrate salt

HRID 429953Notes

Reaction equation

HRID 429953 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][NH2:16])[CH2:9][CH2:8]1.[C:17]([OH:26])(=[O:25])[C@@H:18]([C@H:20]([C:22]([OH:24])=[O:23])[OH:21])[OH:19].C(O)(=O)C(C(C(O)=O)O)O>C(O)C>[C:22]([C@@H:20]([C@H:18]([C:17]([OH:26])=[O:25])[OH:19])[OH:21])([OH:24])=[O:23].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][NH2:16])[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 8752,3-Dihydroxybutanedioic Acid2×HCID 444305L-Tartaric acidHCID 101768154-(2-pyridinyl)-1-Piperidinepropanamine

Product 1

HCID 701512003-[4-(2-Pyridyl)piperidin-1-yl]propylamine l-tartrate salt

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 3-[4-(2-pyridyl)piperidin-1-yl]propylamine, (6), (637.9 g, 3.86 mol) in ethanol (8.5 L) was warmed to 65° C. A solution of L-tartaric acid (637.9 g, 4.25 mol) in ethanol (2.23 L) was added in portions. Approximately 15% of the tartaric acid solution was added and then reaction mixture was aged for 1 hour to afford a thin slurry of crystalline material. The remaining tartaric acid solution was added dropwise. Heating was discontinued and the solution was slowly cooled to ambient temperature overnight. The solids were filtered, rinsed with ethanol (2×1 L) and dried under a stream of nitrogen to afford 3-[4-(2-pyridyl)piperidin-1-yl]propylamine L-tartrate salt, (7), as a pale yellow solid.

Workup

  1. customreaction mixture
  2. customto afford a thin slurry of crystalline material
  3. temperatureHeating
  4. filtrationThe solids were filtered
  5. washrinsed with ethanol (2×1 L)
  6. customdried under a stream of nitrogen

Sources & evidence

ORD record
ord-b42109ac54cf43b2b9777bd9c1d495e6
Source dataset
uspto-grants-2001_11
Patent number
US06320049B1

Reaction notes

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