Methanol → 6,7,8,9-tetrahydro-5H-pyrido[3,2-b]azepine

HRID 1733958Notes

Reaction equation

HRID 1733958 reaction equation
[N:1]1[C:11]2[CH2:10][CH2:9][CH2:8][C:7](=O)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].CO>O1CCCC1>[N:1]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1228303261479-36-5HCID 21226445Aluminium lithium hydride

Product 1

HCID 124131726,7,8,9-tetrahydro-5H-pyrido[3,2-b]azepineYield 70.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.56 g of 5,7,8,9-tetrahydro-6H-pyrido[3,2-b]azepine-6-one, 3.31 g of lithium aluminum hydride in 40 ml of tetrahydrofuran is refluxed for 4 hours. The mixture is cooled (0° C.) and 25 ml of methanol is added dropwise. The mixture is filtered through diatomaceous earth, the filter cake washed with tetrahydrofuran and the filtrate concentrated to dryness under vacuum. Water (50 ml) is added to the residue and the mixture extracted with diethyl ether. The extract is dried (Na2SO4) and filtered through a thin pad of hydrous magnesium silicate (pad washed with) diethyl ether. The filtrate is concentrated under vacuum to give 1.01 g of crystals, m.p. 70°-71° C.

Workup

  1. temperatureis refluxed for 4 hours
  2. additionis added dropwise
  3. filtrationThe mixture is filtered through diatomaceous earth
  4. washthe filter cake washed with tetrahydrofuran
  5. concentrationthe filtrate concentrated to dryness under vacuum
  6. additionWater (50 ml) is added to the residue
  7. extractionthe mixture extracted with diethyl ether
  8. dry with materialThe extract is dried (Na2SO4)
  9. filtrationfiltered through a thin pad of hydrous magnesium silicate (pad washed with) diethyl ether
  10. concentrationThe filtrate is concentrated under vacuum

Sources & evidence

ORD record
ord-8df1eec7647348ebac69b88cf384f641
Source dataset
uspto-grants-1996_07
Patent number
US05532235

Reaction notes

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