Sodium Iodide → HCID 23122017, compound

HRID 1713556Notes

Reaction equation

HRID 1713556 reaction equation
Cl.[C:2]1([C:8]2([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:12]3[CH2:13][N:14]([C:17]([CH:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)=[O:18])[CH2:15][CH2:16][N:11]3[C:10](=[O:25])[O:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl[CH2:41][C:42]([NH2:44])=[O:43]>CN(C)C(=O)C.O>[O:25]=[C:10]1[N:11]2[CH2:16][CH2:15][N:14]([C:17]([CH:19]3[CH2:24][CH2:23][N:22]([CH2:41][C:42]([NH2:44])=[O:43])[CH2:21][CH2:20]3)=[O:18])[CH2:13][CH:12]2[C:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[O:9]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6580ChloroacetamideHCID 11430Potassium CarbonateHCID 23121958HCID 23121958, compound

Product 1

HCID 23122017HCID 23122017, compoundYield 50.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

A solution of hexahydro-1,1-diphenyl-7-[(4-piperidinyl)carbonyl]-3H-oxazolo[3,4-a]pyrazin-3-one hydrochloride (0.15 g, 0.34 mmol), potassium carbonate (0.12 g, 0.87 mmol), sodium iodide (51 mg, 0.34 mmol) and 2-chloroacetamide (38 mg, 0.41 mmol) in N,N-dimethylacetamide (3 mL) was stirred at room temperature for 26 hours. The reaction solution was diluted with water, and the mixture was extracted with ethyl acetate-tetrahydrofuran. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solid was filtered off, and the filtrate was concentrated and dried to a solid. The residue was recrystallized from ethanol to obtain the title compound (80 mg, yield 50%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate-tetrahydrofuran
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe solid was filtered off
  5. concentrationthe filtrate was concentrated
  6. customdried to a solid
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-fe5b453e5943420c9e1a00cba96abfb0
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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