Ethylenediamine → 4'-(n-2-Aminoethyl)aminospiro[1-azabicyclo[2.2.2]octane-3,2'(3'h)-furo[2,3-b]pyridine]

HRID 48525Notes

Reaction equation

HRID 48525 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[O:8][C:9]3([CH:15]4[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]4)[CH2:11]3)[CH2:10][C:3]=12.[CH2:18]([NH2:21])[CH2:19][NH2:20]>>[NH2:20][CH2:19][CH2:18][NH:21][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[O:8][C:9]3([CH:15]4[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]4)[CH2:11]3)[CH2:10][C:3]=12

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 100377734'-chlorospiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]

Product 1

HCID 117781134'-(n-2-Aminoethyl)aminospiro[1-azabicyclo[2.2.2]octane-3,2'(3'h)-furo[2,3-b]pyridine]

Procedure

A solution of 74 mg (0.295 mmol) of 4′-chlorospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] in 10 mL of ethylenediamine was heated to reflux under a nitrogen atmosphere and stirred for 4 days. Upon cooling to ambient temperature, the solvent was removed in vacuo. The residue was dissolved in 20 mL of saturated aqueous sodium carbonate and extracted with chloroform (3×25 mL). The combined organic extract was dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title compound as a dark oil, 80 mg (100%): electrospray MS (m/z, relative intensity) 275 ([MH]+).

Workup

  1. temperatureto reflux under a nitrogen atmosphere
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in 20 mL of saturated aqueous sodium carbonate
  4. extractionextracted with chloroform (3×25 mL)
  5. extractionThe combined organic extract
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-94349ec1c95c4d0393ddc99632c72773
Source dataset
uspto-grants-2004_03
Patent number
US06703502B2

Reaction notes

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