Hydrochloric Acid → Zaleplon

HRID 1394392Notes

Reaction equation

HRID 1394392 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.N[C:21]1[C:25]([C:26]#[N:27])=C[NH:23][N:22]=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:23]3[N:22]=[CH:21][C:25]([C:26]#[N:27])=[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 178510443HCID 178510443, compound

Product 1

HCID 5719ZaleplonYield 91.8%

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 (1.08 g, 0.01 mol) were dissolved in the mixture of water (35 cm3) and methanol (20 cm3). Concentrated (37%) hydrochloride acid (1.0 cm3, 0.012 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 that formed was collected, washed with water and dried at about 60° C. to yield zaleplon (2.80 g, 91.8%) in 98.69% 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 that formed
  4. customwas collected
  5. washwashed with water
  6. customdried at about 60° C.

Sources & evidence

ORD record
ord-4bb21c26cde345568e0c837895ff5bd3
Source dataset
uspto-grants-2008_03
Patent number
US07348429B2

Reaction notes

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