Aluminium lithium hydride → HCID 66781649, compound

HRID 1360154Notes

Reaction equation

HRID 1360154 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH3:17])[NH:14][CH:13]([C:15]#[N:16])[CH2:12][O:11][CH2:10]2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2([CH3:17])[NH:14][CH:13]([CH2:15][NH2:16])[CH2:12][O:11][CH2:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 667820763-Morpholinecarbonitrile, 5-(4-methoxyphenyl)-5-methyl-

Product 1

HCID 66781649HCID 66781649, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.25 mmol of 5-(4-methoxyphenyl)-5-methylmorpholin-3-carbonitrile (Example 3f2) in 10 ml of tetrahydrofuran is cooled to 0-5° C. in an ice bath. 6.75 mmol of lithium aluminium hydride are added in portions, and the reaction mixture is then stirred at room temperature for 1 hour. The reaction mixture is quenched with 0.5 ml of methanol and mixed with 40 ml of dichloromethane and 0.060 g of solid potassium carbonate, and 0.60 ml of water. The suspension is filtered through Hyflo and the filter cake is washed with dichloromethane. The filtrate is evaporated. The title compound is obtained as a colourless oil from the residue by flash chromatography (SiO2 60F). Rf=0.26 (dichloromethane-methanol-25% aqueous ammonia solution 200:20:1), Rt=2.13 (gradient I)

Workup

  1. customis cooled to 0-5° C. in an ice bath
  2. customThe reaction mixture is quenched with 0.5 ml of methanol
  3. additionmixed with 40 ml of dichloromethane and 0.060 g of solid potassium carbonate, and 0.60 ml of water
  4. filtrationThe suspension is filtered through Hyflo
  5. washthe filter cake is washed with dichloromethane
  6. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-037755c0fa0a421588730efb73f169d5
Source dataset
uspto-grants-2011_02
Patent number
US07879847B2

Reaction notes

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