Sodium Carbonate → HCID 69430529, compound

HRID 1352714Notes

Reaction equation

HRID 1352714 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 or 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): δ 26.6, 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 or 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-4057498c7cba48569cd84f856f112566
Source dataset
uspto-grants-2007_05
Patent number
US07220753B2

Reaction notes

Loading…