Ethanol → 2-[(2-Oxopiperazin-1-yl)methyl]indane-5-carbonitrile

HRID 1466043Notes

Reaction equation

HRID 1466043 reaction equation
ClC[C:3]([N:5]([CH2:16][CH:17]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:26]#[N:27])[CH:23]=2)[CH2:18]1)[CH2:6][CH2:7][NH:8][C:9](=O)OC(C)(C)C)=[O:4].CCO.C([O-])([O-])=O.[K+].[K+]>Cl.O1CCOCC1>[O:4]=[C:3]1[CH2:9][NH:8][CH2:7][CH2:6][N:5]1[CH2:16][CH:17]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:26]#[N:27])[CH:23]=2)[CH2:18]1

Participants

5

Reactant 3

HCID 702EthanolHCID 11430Potassium CarbonateHCID 131732679tert-Butyl (2-{(chloroacetyl)[(5-cyano-2,3-dihydro-1H-inden-2-yl)methyl]amino}ethyl)carbamate

Product 1

HCID 895250452-[(2-Oxopiperazin-1-yl)methyl]indane-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A mixture of tert-Butyl (2-{(chloroacetyl)[(5-cyano-2,3-dihydro-1H-inden-2-yl)methyl]amino}ethyl)carbamate (350 mg, 0.9 mmol) in HCl/dioxane (20 mL) was stirred at RT for 12 hours and then concentrated to dryness. To the residue was added 20 mL EtOH and K2CO3 (500 mg, 3.7 mmol). The resulting mixture was heated to reflux for 4 hrs before cooled to RT and filtered. The filtrate was concentrate and the residue was partitioned between EtOAc and water. The organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated to dryness to give 2-[(2-Oxopiperazin-1-yl)methyl]indane-5-carbonitrile. MS m/z: 256 [M+1]+.

Workup

  1. concentrationconcentrated to dryness
  2. temperatureThe resulting mixture was heated
  3. temperatureto reflux for 4 hrs
  4. temperaturebefore cooled to RT
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrate
  7. customthe residue was partitioned between EtOAc and water
  8. washThe organic layer was washed with brine
  9. dry with materialdried over anhydrous Na2SO4
  10. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-af1b562feedd4379b7bde79cdc20bbe0
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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