Water → HCID 53989671, compound

HRID 1283557Notes

Reaction equation

HRID 1283557 reaction equation
[CH3:1][C:2]([N:9]([CH3:11])[CH3:10])([CH2:5][CH2:6][CH2:7][CH3:8])[C:3]#[N:4].O>CCOCC>[CH3:1][C:2]([N:9]([CH3:10])[CH3:11])([CH2:5][CH2:6][CH2:7][CH3:8])[CH2:3][NH2:4]

Participants

4

Reactant 2

HCID 962WaterHCID 21409853HCID 21409853, compound

Product 1

HCID 53989671HCID 53989671, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of 2-methyl-2-dimethylamino-hexanenitrile (7.70 g.,) in dry ether (100 ml.) was added dropwise to a stirred solution of sodium dihydro-bis(2-methoxy-ethoxy)aluminate (43.3 g., 70% solution in benzene, 25% excess) in dry ether (100 ml.) under nitrogen with ice water cooling. The solution was refluxed overnight under nitrogen and allowed to cool. Ether (200 ml.) was added, followed by dropwise addition of excess water with ice-water cooling to destroy excess reducing reagent. The mixture was filtered on hyflo and the filtrates extracted with ether (4 × 100 ml.). The combined ether extracts were washed with water (4 × 200 ml.), dried (Na2SO4) and evaporated leaving a colourless oil. Distillation of the oil afforded 2-methyl-2-dimethylamino-hexylamine as a colourless liquid (4.808 g., 61%) b.p. 86-88/12 mm..

Workup

  1. temperatureThe solution was refluxed overnight under nitrogen
  2. temperatureto cool
  3. customto destroy excess
  4. filtrationThe mixture was filtered on hyflo
  5. extractionthe filtrates extracted with ether (4 × 100 ml.)
  6. washThe combined ether extracts were washed with water (4 × 200 ml.)
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customleaving a colourless oil
  10. distillationDistillation of the oil

Sources & evidence

ORD record
ord-88e7e71db37241569c8916a5f6c03f5e
Source dataset
uspto-grants-1976_08
Patent number
US03975443

Reaction notes

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