Sodium Cyanide → HCID 69430029, compound

HRID 1458782Notes

Reaction equation

HRID 1458782 reaction equation
CS(O[CH2:6][CH:7]1[CH2:22][N:11]2[CH2:12][CH2:13][N:14]([C:16]3[N:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH2:15][CH:10]2[CH2:9][CH2:8]1)(=O)=O.[C-:23]#[N:24].[Na+].C(=O)(O)[O-].[Na+]>CN(C=O)C>[N:17]1[CH:18]=[CH:19][CH:20]=[N:21][C:16]=1[N:14]1[CH2:13][CH2:12][N:11]2[CH2:22][CH:7]([CH2:6][C:23]#[N:24])[CH2:8][CH2:9][CH:10]2[CH2:15]1

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 516892Sodium BicarbonateHCID 19963213HCID 19963213, compound

Product 1

HCID 69430029HCID 69430029, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 38.1 g (117 mmol) of (7SR,9aSR)-7-(methanesulfonyloxy)methyl-2-(pyrimidin-2-yl)-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine (prepared according to U.S. Pat. No. 5,122,525) and 6.01 g (122 mmol) of sodium cyanide in 500 mL of dry DMF was heated at 110° C. for 16 h. The mixture was cooled to room temperature, 10 mL of saturatic sodium bicarbonate was added and the mixture concentrated in vacuo. Water (1000 mL) and ethyl acetate (1000 mL) were added to the solid residue, the pH was adjusted to 11, and the layers were separated. The organic phase was washed with water (2×), dried (sodium sulfate), filtered and evaporated. Recrystalization from ethyl acetate-hexane gave 14.5 g of [(7SR,9aSR)-2-(pyrimidin-2-yl)-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazin-7-yl]acetonitrile. 13C NMR (CDCl3): d 19.5, 24.1, 26.9, 31.3, 33.1, 43.6, 48.9, 54.5, 109.8, 119.8, 157.7, 161.4.

Workup

  1. concentrationthe mixture concentrated in vacuo
  2. additionWater (1000 mL) and ethyl acetate (1000 mL) were added to the solid residue
  3. customthe layers were separated
  4. washThe organic phase was washed with water (2×)
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. customevaporated
  8. customRecrystalization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-2bb62b56d16e461e9e8760b3caa49473
Source dataset
uspto-grants-1998_12
Patent number
US05852031

Reaction notes

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