Hydrochloric Acid → Zaleplon

HRID 1394394Notes

Reaction equation

HRID 1394394 reaction equation
C[N:2]([CH3:19])[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[C:9]([N:13]([CH2:17][CH3:18])[C:14](=[O:16])[CH3:15])[CH:10]=[CH:11][CH:12]=1)=O.Cl.N[C:22]1[C:26]([C:27]#[N:28])=C[NH:24][N:23]=1.Cl>O.CO>[CH3:18][CH2:17][N:13]([C:14]([CH3:15])=[O:16])[C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:5]2[N:24]3[N:23]=[CH:22][C:26]([C:27]#[N:28])=[C:19]3[N:2]=[CH:3][CH:4]=2)[CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 53395302N-(3-(3-(Dimethylamino)-1-oxo-2-propenyl)phenyl)-N-ethylacetamideHCID 178479187HCID 178479187, compound

Product 1

HCID 5719ZaleplonYield 96.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-ethylacetamide (2.6 g, 0.01 mol) and 3-amino-4-cyanopyrazole-hydrochloride (1.44 g, 0.01 mol) were dissolved in the mixture of water (35 cm3) and methanol (20 cm3). Concentrated (37%) hydrochloric acid (0.83 cm3, 0.01 mol) was then added and the mixture was stirred at room temperature for about 2 hours. The reaction mixture was then cooled to about 5° C. and the crystalline product formed was collected, washed with water and dried at about 60° C. to yield zaleplon (2.93 g, 96.1%) in 99.16% purity as determined by HPLC.

Workup

  1. additionwas then added
  2. temperatureThe reaction mixture was then cooled to about 5° C.
  3. customthe crystalline product formed
  4. customwas collected
  5. washwashed with water
  6. customdried at about 60° C.

Sources & evidence

ORD record
ord-b53fab70bfa84bb693e0654ee89426e7
Source dataset
uspto-grants-2008_03
Patent number
US07348429B2

Reaction notes

Loading…