Sodium Carbonate → HCID 69433632, compound

HRID 1977066Notes

Reaction equation

HRID 1977066 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 22940604HCID 22940604, compound

Product 1

HCID 69433632HCID 69433632, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

A mixture of 1.35 g (5.56 mmol) of (7R,9aS)-7-hydroxymethyl-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine dihyrochloride (Preparation 1), 4.11 g (27.8 mmol) of 2,5-dichloropyridine, 2.94 g (27.8 mmol) of sodium carbonate and 60 mL of isoamyl alcohol was heated at reflux for 48 h. The mixture was cooled and the solvent removed in vacuo. Purification by flash silica gel chromatography with 95:5 chloroform: methanol gave 1.02 g (65%) of the title compound. mp (base) 139.0-140.5° C. 13C NMR (CDCl3): δ26.8, 29.1, 39.1, 45.3, 50.8, 54.6, 58.6, 60.6, 66.2, 107.7, 120.1, 137.1,146.2, 157.6.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 48 h
  3. temperatureThe mixture was cooled
  4. customthe solvent removed in vacuo
  5. customPurification by flash silica gel chromatography with 95:5 chloroform

Sources & evidence

ORD record
ord-ed67d73456c44aaa914fc89218212eff
Source dataset
uspto-grants-2001_05
Patent number
US06231833B1

Reaction notes

Loading…