HCID 18933638, compound → HCID 18933625, compound

HRID 1598311Notes

Reaction equation

HRID 1598311 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]([CH2:16][CH2:17][O:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:20]=1[C:21]#[N:22])[CH3:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([N:14]([CH2:16][CH2:17][O:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:20]=1[CH2:21][NH2:22])[CH3:15])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 18933638HCID 18933638, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18933625HCID 18933625, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of lithium aluminium hydride in THF (790 ml of a 1M solution) was stirred under nitrogen at ambient temperature and diluted with dry THF (1 l) and then a solution of 2-[2-(N-benzyl-N-methylamino)ethoxy]-6-chlorobenzonitrile (237 g) in dry THF (200 ml) was added over 30 minutes. When approximately three-quarters of the solution had been added an exotherm was observed and this was checked by cooling the reaction mixture in an ice/water bath. The mixture was stirred for 1 hour after the addition and then quenched by the cautious addition of water (30 ml), 15% sodium hydroxide solution (30 ml) and water (90 ml). The mixture was diluted with ethyl acetate (1 l) and filtered through a filter aid. The filter aid was boiled with ethyl acetate (2×500 ml) and filtered through a filter aid. The combined filtrates were dried and evaporated to give 2-[2-(N-benzyl-N-methylamino)ethoxy]-6-chlorobenzylamine as an oil.

Workup

  1. additionWhen approximately three-quarters of the solution had been added an exotherm
  2. temperatureby cooling the reaction mixture in an ice/water bath
  3. additionafter the addition
  4. customquenched by the cautious addition of water (30 ml), 15% sodium hydroxide solution (30 ml) and water (90 ml)
  5. additionThe mixture was diluted with ethyl acetate (1 l)
  6. filtrationfiltered through a filter aid
  7. filtrationfiltered through a filter aid
  8. customThe combined filtrates were dried
  9. customevaporated

Sources & evidence

ORD record
ord-d470208791a940e3aef22e68e6d9192f
Source dataset
uspto-grants-1998_04
Patent number
US05736568

Reaction notes

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