Aluminium lithium hydride → HCID 66781649, compound

HRID 1095320Notes

Reaction equation

HRID 1095320 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 60 F). 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-d9cfa64b0b024020a51bff8249310f53
Source dataset
uspto-grants-2012_03
Patent number
US08138176B2

Reaction notes

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