Piperidine → 3-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine

HRID 35042Notes

Reaction equation

HRID 35042 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][CH2:8][CH2:9][N:10]1C(=O)C2C(=CC=CC=2)C1=O)=O.[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>C(OCC)(=O)C.[Pd]>[N:24]1([CH2:1][C:3]2[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=2)[O:6][CH2:7][CH2:8][CH2:9][NH2:10])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 2

HCID 8082PiperidineHCID 128106403-(3-(1,3-Dioxoisoindolin-2-yl)propoxy)benzaldehyde

Product 1

HCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amineYield 77.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-[3-[3-Formylphenoxy]propyl]-1H-isoindole-1,3-dione (50 g) and piperidine (20.7 g) in ethyl acetate (750 ml) were hydrogenated over 10% palladium/carbon catalyst. The catalyst was removed by filtration and the solvent evaporated and hydrazine hydrate (40 ml) was added to an ethanolic solution of the residue at 25°. After 67 hr the reaction mixture was diluted with ether, filtered and the filtrate was distilled to give the title compound as a colourless oil (31.05 g) b.p. 154°-8°/0.15 mm. TLC silica, methanol/0.88 ammonia 80:1, Rf 0.2.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated
  3. additionhydrazine hydrate (40 ml) was added to an ethanolic solution of the residue at 25°
  4. additionAfter 67 hr the reaction mixture was diluted with ether
  5. filtrationfiltered
  6. distillationthe filtrate was distilled

Sources & evidence

ORD record
ord-901673bcad964d5ba16d91cec748ed95
Source dataset
uspto-grants-1988_08
Patent number
US04764612

Reaction notes

Loading…