Ammonium Chloride → HCID 66914826, compound

HRID 880448Notes

Reaction equation

HRID 880448 reaction equation
[CH3:1][N:2]1[C:7](=O)[CH2:6][N:5]2[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:11]=[C:4]2[CH2:3]1.[Cl-].[NH4+]>O1CCCC1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]2[CH:9]=[C:10]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:11]=[C:4]2[CH2:3]1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 66914859HCID 66914859, compound

Product 1

HCID 66914826HCID 66914826, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-dimethyl sulfide complex (0.25 mL, 2.6 mmol) was added to cold tetrahydrofuran (6 mL) and stirred for 10 min. 2-Methyl-7-phenyl-1,2-dihydropyrrolo[1,2-a]pyrazin-3-one (180 mg, 0.8 mmol) was added, and the reaction mixture allowed to warm to room temperature and stirred for 3 h. The mixture was poured slowly into saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with water then brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the crude compound. Purification by column chromatography over silica gel (100-200 mesh) using 8% ethyl acetate in petroleum ether afforded 2-methyl-7-phenyl-3,4-dihydro-1H-pyrrolo[1,2-a]pyrazine (110 mg, 64%) as a solid.

Workup

  1. stirringstirred for 3 h
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialbrine, dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give the crude compound
  8. customPurification by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-e50a3b7b1c64453dbdaae2f9a16000b3
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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