Aluminium lithium hydride → HCID 23301889, compound

HRID 1953004Notes

Reaction equation

HRID 1953004 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]([CH3:24])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:11][CH:10]=1)#[N:8]>O1CCCC1>[C:18]1([CH2:17][N:16]([CH2:15][C:12]2[CH:13]=[CH:14][C:9]([CH2:7][NH2:8])=[CH:10][CH:11]=2)[CH3:24])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 23301867HCID 23301867, compound

Product 1

HCID 23301889HCID 23301889, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 1.9 g (0.05 Mol) of lithium aluminium hydride in 70 ml of anhydrous tetrahydrofuran was added dropwise, at ambient temperature, a solution of 12.1 g (0.051 Mol) of 4-cyano-N-methyl-N-(phenylmethyl)benzenemethanamine in 30 ml of dry tetrahydrofuran and the mixture was then heated to 60° C. for 3 hours and refluxed for 2 hours. A further 0.5 g of lithium aluminium hydride were added and the mixture was refluxed for another 3 hours. After working up in the usual way and purification by column chromatography (Baker; 0.03-0.06 mm; dichloromethane/methanol/cyclohexane/conc. aqueous ammonia=68/15/15/2 (v/v/v/v)) 10.2 g (83% of theory) of a colourless oil were obtained.

Workup

  1. additionwas added dropwise, at ambient temperature
  2. temperaturerefluxed for 2 hours
  3. temperaturethe mixture was refluxed for another 3 hours
  4. customAfter working up in the usual way and purification by column chromatography (Baker; 0.03-0.06 mm; dichloromethane/methanol/cyclohexane/conc. aqueous ammonia=68/15/15/2 (v/v/v/v)) 10.2 g (83% of theory) of a colourless oil
  5. customwere obtained

Sources & evidence

ORD record
ord-661cb26c2fcd44ad8da539803a8f1590
Source dataset
uspto-grants-2000_09
Patent number
US06114390

Reaction notes

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