Water → HCID 64135446, compound

HRID 2088868Notes

Reaction equation

HRID 2088868 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:8][C:9]1[CH:17]=[CH:16][C:12]([CH2:13][CH2:14]N)=[CH:11][CH:10]=1.O>C(O)CCC>[Br:8][C:9]1[CH:17]=[CH:16][C:12]([CH2:13][CH2:14][C:7]2[C:2]([NH2:1])=[N:3][CH:4]=[CH:5][CH:6]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 104392-AminopyridineHCID 533915p-Bromophenethylamine

Product 1

HCID 64135446HCID 64135446, compoundYield 24.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
230 °C

Procedure

In a sealed tube, a mixture of 1.9 g (20.4 mmol) of 2-aminopyridine and 6.1 g (30.6 mmol) of 4-bromophenethylamine dissolved in butanol (10 ml) is heated at 230° C. for 1 hour by microwave. The mixture, cooled to room temperature, is poured into water (50 ml) and extracted with ethyl acetate (3×100 ml), and the combined organic phases are dried over sodium sulfate, filtered and concentrated. The residue is purified by flash chromatography on a column of silica gel (eluent: dichloromethane/ethyl acetate, from 0% to 50% ethyl acetate). 1.4 g of product are obtained in the form of a white powder. Yield: 24%. Melting point: 71° C. MH+: 278.1 (tr: 3.71 min., condition 1).

Workup

  1. temperatureThe mixture, cooled to room temperature
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. dry with materialthe combined organic phases are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography on a column of silica gel (eluent: dichloromethane/ethyl acetate, from 0% to 50% ethyl acetate)

Sources & evidence

ORD record
ord-81b7b9c127374021bda5c1fbd5e92d92
Source dataset
uspto-grants-2013_05
Patent number
US08436011B2

Reaction notes

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