Ammonia → HCID 19775889, compound

HRID 373787Notes

Reaction equation

HRID 373787 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[O:5][C:6]1[CH:16]=[CH:15][C:9]([O:10][CH2:11][C:12](=O)[CH3:13])=[CH:8][CH:7]=1.[NH3:20].[H][H]>CO.[Ni]>[NH2:20][CH:12]([CH3:13])[CH2:11][O:10][C:9]1[CH:15]=[CH:16][C:6]([O:5][C:4]2[CH:17]=[CH:18][CH:19]=[C:2]([Cl:1])[CH:3]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 19808413HCID 19808413, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19775889HCID 19775889, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

51 g of 1-[4-(3-chlorophenoxy)-phenoxy]-2-propanone are dissolved in 510 ml of methanol in an autoclave, and 10 g of Raney nickel are added. 31 g of liquid ammonia are introduced, and then hydrogen gas is introduced under pressure. The reaction mixture is hydrogenated at 50 bar and +40° C.-45° C. for 2 hours. The reaction mixture is then filtered through diatomaceous earth and the solvent is distilled off completely in vacuo. The crude product is chromatographed over silica gel (eluant: diethyl ether/methanol, 9:1), yielding pure 2-amino-1-[4-(3-chlorophenoxy)-phenoxy]-propane in the form of a colourless, oily liquid, n20D : 1.5743.

Workup

  1. additionare added
  2. filtrationThe reaction mixture is then filtered through diatomaceous earth
  3. distillationthe solvent is distilled off completely in vacuo
  4. customThe crude product is chromatographed over silica gel (eluant: diethyl ether/methanol, 9:1)

Sources & evidence

ORD record
ord-e666683a1e2e48d5ac7f6bf377f4a093
Source dataset
uspto-grants-1992_11
Patent number
US05166153

Reaction notes

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