Ammonia → HCID 20433009, compound

HRID 258736Notes

Reaction equation

HRID 258736 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-d37be1a0dcae463783e2e23209e544b6
Source dataset
uspto-grants-1977_07
Patent number
US04034040

Reaction notes

Loading…