N-[6-[2-(2-Pyridinyl)ethoxy]hexyl]benzenemethanamine → HCID 15166946, compound

HRID 2108042Notes

Reaction equation

HRID 2108042 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16]CC1C=CC=CC=1>C(O)C.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2:16]

Participants

4

Reactant 1

HCID 19876743N-[6-[2-(2-Pyridinyl)ethoxy]hexyl]benzenemethanamine

Product 1

HCID 15166946HCID 15166946, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A solution of N-[6-[2-(2-pyridinyl)ethoxy]hexyl]benzenemethanamine (2.00 g) in ethanol (10 ml) was added to a pre-hydrogenated suspension of 10% palladium on carbon (50% paste, 800 mg) in ethanol (120 ml) and hydrogenated at room temperature and pressure. The catalyst was removed by filtration through hyflo and the solvent evaporated in vacuo. The residual oil was purified by FCC eluting with System A (39:10:1→32:17:1) to afford the title compound as a colourless liquid (0.99 g), t.l.c. (System A 39:10:1) Rf 0.16.

Workup

  1. customThe catalyst was removed by filtration through hyflo
  2. customthe solvent evaporated in vacuo
  3. customThe residual oil was purified by FCC
  4. washeluting with System A (39:10:1→32:17:1)

Sources & evidence

ORD record
ord-2b180ecc1d134eb1b41fedf4ff3eb168
Source dataset
uspto-grants-1990_06
Patent number
US04937251

Reaction notes

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