Ammonia → HCID 20433009, compound

HRID 371792Notes

Reaction equation

HRID 371792 reaction equation
[CH2:1]([O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:11]=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH3:23]>[Ni].C(O)C.[H][H]>[CH2:1]([O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:11][NH2:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 2

HCID 222AmmoniaHCID 118229373,4-dihexyloxybenzaldehyde

Product 1

HCID 20433009HCID 20433009, compoundYield 52.1%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

Raney nickel (500 mg.), 3,4-dihexoxybenzaldehyde (6.12 g., 0.02 M) and ammonia (3.0 g., 0.177 M) in ethanol (100 ml.) are charged into a Paar shaker and hydrogenated at 40° C and an initial pressure of 51 psi. When approximately 20 psi drop in hydrogen pressure is observed, about 24 hours, the contents are removed and filtered. The filtrate is concentrated in vacuo to an amber oil which is dissolved in ethyl acetate (50 ml.). The solution is treated with ethyl acetate saturated with hydrogen chloride (100 ml.) and the resulting white hydrochloride salt collected; 3.7 g., m.p. 205°-206° C. The salt is then partitioned between chloroform (100 ml.) and saturated sodium bicarbonate solution (50 ml.). The chloroform phase is separated, washed with water (50 ml.), dried (Na2SO4) and concentrated to give 3,4-dihexoxybenzylamine as an oil; 3.2 g., 52.1% yield.

Workup

  1. customthe contents are removed
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated in vacuo to an amber oil which
  4. dissolutionis dissolved in ethyl acetate (50 ml.)
  5. additionThe solution is treated with ethyl acetate saturated with hydrogen chloride (100 ml.)
  6. customthe resulting white hydrochloride salt collected
  7. customThe salt is then partitioned between chloroform (100 ml.) and saturated sodium bicarbonate solution (50 ml.)
  8. customThe chloroform phase is separated
  9. washwashed with water (50 ml.)
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-af2ebda68d144d81bac7da12ed10244a
Source dataset
uspto-grants-1978_05
Patent number
US04087552

Reaction notes

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