Ammonia → HCID 20560975, compound

HRID 1155500Notes

Reaction equation

HRID 1155500 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)[CH:5]=[N:4][CH:3]=1.N.[BH3-]C#[N:18].[Na+].Cl>CO>[ClH:1].[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([NH2:18])[CH2:10][CH2:9]2)[CH:5]=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 128022151-(6-Chloropyrazin-2-yl)piperidin-4-one

Product 1

HCID 20560975HCID 20560975, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 17.1 g (81 mmol) 6-chloro-2-(4-oxopiperidino)pyrazine in 250 ml methanol which has been saturated with gaseous NH3 is added 62.4 g (0.81 mol) NH4OAc and 5.0 g (80 mmol) NaCNBH3. After stirring at 20°-25° C. for 60 hours, the MeOH is removed in vacuo. Water is added to the residue, and the pH is adjusted to 14. The product is extracted into ethyl acetate which is dried and concentrated. Chromatography of the residue over silica gel, eluting with 5% MeOH/CHCl3 saturated with NH3, gives the product base which is converted to the hydrochloride salt with ethanolic HCl. Recrystallization from water/acetone affords the desired product, m.p. 291° C. (dec.).

Workup

  1. customthe MeOH is removed in vacuo
  2. additionWater is added to the residue
  3. extractionThe product is extracted into ethyl acetate which
  4. customis dried
  5. concentrationconcentrated
  6. washChromatography of the residue over silica gel, eluting with 5% MeOH/CHCl3 saturated with NH3
  7. customgives the product base which
  8. customRecrystallization from water/acetone

Sources & evidence

ORD record
ord-fafb320e31184145af10aa444e9c7dd2
Source dataset
uspto-grants-1981_11
Patent number
US04302455

Reaction notes

Loading…