Aluminium lithium hydride → HCID 59438542, compound

HRID 2177480Notes

Reaction equation

HRID 2177480 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH2:7][C:8]1([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[CH2:13][N:12]([CH3:14])[C:11](=O)[CH2:10][CH2:9]1>C1COCC1>[Cl:22][C:18]1[CH:17]=[C:16]([C:8]2([NH2:7])[CH2:9][CH2:10][CH2:11][N:12]([CH3:14])[CH2:13]2)[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59438473HCID 59438473, compound

Product 1

HCID 59438542HCID 59438542, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of 20 mg (0.494 mmol) LiAlH4 in 0.5 ml THF was added dropwise a solution of 59 mg (0.247 mmol) rac-5-amino-5-(3-chloro-phenyl)-1-methyl-piperidin-2-one in 0.6 ml THF at room temperature. The mixture was refluxed for 30 minutes. The mixture was cooled in an ice bath and quenched carefully with 20 ul water, 20 ul 5N NaOH and finally 60 ul water. Ethyl acetate was added. The mixture was filtered and the filtrate was concentrated in vacuo to provide 48 mg (86%) of the title compound as a colorless oil. MS (m/e): 225.2 (MH+).

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. temperatureThe mixture was cooled in an ice bath
  3. customquenched carefully with 20 ul water, 20 ul 5N NaOH and finally 60 ul water
  4. additionEthyl acetate was added
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-da272b485f9c45fab26aef4af96b36d7
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

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