Aluminium lithium hydride → HCID 28721148, compound

HRID 1159892Notes

Reaction equation

HRID 1159892 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([C:13](=O)[CH2:14][CH2:15][C:16]2[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1>C1COCC1>[N:7]1([CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 28713295HCID 28713295, compound

Product 1

HCID 28721148HCID 28721148, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1M lithium aluminum hydride in THF (2.6 mL) was injected into a stirred suspension of {3-[3-(4-morpholinyl)-3-oxopropyl]phenyl}amine (120 mg, 0.51 mmol) in anhydrous THF (5 mL). The reaction was refluxed for 1 h under nitrogen. The suspension was cooled to 0° C. and quenched by careful addition of 1N NaOH. The base was added until gas evolution stopped. The reaction was concentrated to a white solid under vacuum, triturated with diethyl ether and filtered. The filtrate was concentrated under vacuum to 113 mg (89%) of the title compound, a clear oil. MS (ESI): M+H=221.17.

Workup

  1. temperatureThe reaction was refluxed for 1 h under nitrogen
  2. customquenched by careful addition of 1N NaOH
  3. additionThe base was added until gas evolution
  4. concentrationThe reaction was concentrated to a white solid under vacuum
  5. customtriturated with diethyl ether
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under vacuum to 113 mg (89%) of the title compound

Sources & evidence

ORD record
ord-df7560e2b1b048be8e58430e00bd5042
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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