Sodium hydride → 3-(6,7,8,9-Tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)-propylamine

HRID 993245Notes

Reaction equation

HRID 993245 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[N:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][NH2:15])=[CH:7][CH:6]=1.[H-].[Na+]>>[N:10]1[C:9]2[NH:15][CH2:14][CH2:13][CH2:12][CH2:11][C:8]=2[CH:7]=[CH:6][C:5]=1[CH2:4][CH2:3][CH2:2][NH2:1]

Participants

3

Reactant 2

HCID 24758Sodium hydrideHCID 184089864-[6-(3-Amino-propyl)-pyridin-3-yl]-butyl amine

Product 1

HCID 184089753-(6,7,8,9-Tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)-propylamineYield 26.9%

Procedure

A mixture of 3-5 (3.0 g, 14.5 mmol) and NaH (1.7 g of a 60% weight dispersion in mineral oil, 47 mmol) in xylenes (100 mL) was purged with argon for 30 min, and then heated at reflux for 72 hours. The mixture was cooled, quenched with ethanol, diluted with 10% aqueous potassium carbonate and extracted with ethyl acetate. The organics were dried over MgSO4 and concentrated to an oil. The residue was chromatographed on silica gel (15:10:1:1 EtOAc/EtOH/NH4OH/H2O) to give 800 mg of 3-6 as a yellow oil.

Workup

  1. customwas purged with argon for 30 min
  2. temperatureheated
  3. temperatureat reflux for 72 hours
  4. temperatureThe mixture was cooled
  5. customquenched with ethanol
  6. additiondiluted with 10% aqueous potassium carbonate
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organics were dried over MgSO4
  9. concentrationconcentrated to an oil
  10. customThe residue was chromatographed on silica gel (15:10:1:1 EtOAc/EtOH/NH4OH/H2O)

Sources & evidence

ORD record
ord-60ab0d9af6e24d1ea734ca09ee3fe36f
Source dataset
uspto-grants-2002_10
Patent number
US06472403B2

Reaction notes

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