Ethanol → HCID 89526020, compound

HRID 1466037Notes

Reaction equation

HRID 1466037 reaction equation
ClC[C:3]([N:5]([CH2:16][CH:17]1[C:25]2[C:20](=[CH:21][C:22]([C:26]#[N:27])=[CH:23][CH:24]=2)[CH2:19][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[C:25]2[C:20](=[CH:21][C:22]([C:26]#[N:27])=[CH:23][CH:24]=2)[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 702EthanolHCID 11430Potassium CarbonateHCID 131732676HCID 131732676, compound

Product 1

HCID 89526020HCID 89526020, compound

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A mixture of tert-Butyl (2-{(chloroacetyl)[(5-cyano-2,3-dihydro-1H-inden-1-yl)methyl]amino}ethyl)carbamate (125 mg, 0.32 mmol) in HCl/dioxane (20 mL) was stirred at RT for 12 hours and then concentrated to dryness. To the residue was added 2 mL EtOH and K2CO3 (300 mg, 2.0 mmol). The resulting mixture was heated to reflux for 4 hours 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 1-[(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 hours
  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-751ac2536f854567b6f99ae6db87095b
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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