Sodium Carbonate → HCID 69430529, compound

HRID 1977065Notes

Reaction equation

HRID 1977065 reaction equation
Cl.Cl.[OH:3][CH2:4][C@@H:5]1[CH2:14][N:9]2[CH2:10][CH2:11][NH:12][CH2:13][C@@H:8]2[CH2:7][CH2:6]1.Cl[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CC(C)C>[OH:3][CH2:4][C@@H:5]1[CH2:14][N:9]2[CH2:10][CH2:11][N:12]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=3)[CH2:13][C@@H:8]2[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 276852,5-DichloropyridineHCID 22972877HCID 22972877, compound

Product 1

HCID 69430529HCID 69430529, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

A mixture of 2.5 g (10.3 mmol) of (7S,9aS)-7-hydroxymethyl-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine dihydrochloride, 7.62 g (51.5 mmol) of 2,5-dichloropyridine, 5.45 g (51.5 mmol) of sodium carbonate and 100 mL of isoamyl alcohol was heated at reflux for 72 h. The mixture was cooled, the mixture filtered to remove solids and the solvent evaporated in vacuo. Purification by flash silica gel chromatography using 95:5 chloroform:methanol gave 1.72 g (59%) of the title compound. mp (base) 61-62° C. 13C NMR (base, CDCl3): δ26.6, 27.2, 34.3, 45.4, 50.9, 54.6, 58.4, 60.5, 68.0, 107.7, 120.1, 137.1, 146.2, 157.5. HRMS calcd for C14H20ClN3O: 281.1295, found: 281.1298.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 72 h
  3. temperatureThe mixture was cooled
  4. filtrationthe mixture filtered
  5. customto remove solids
  6. customthe solvent evaporated in vacuo
  7. customPurification by flash silica gel chromatography

Sources & evidence

ORD record
ord-5a22356eaea54c15aff56f60e08fe4b2
Source dataset
uspto-grants-2001_05
Patent number
US06231833B1

Reaction notes

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