Acetic Acid → 2,3,4,9-tetrahydro-1H-beta-carbolin-6-ol hydrochloride

HRID 6739

Reaction equation

HRID 6739 reaction equation
[ClH:1].[NH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:14])[CH:12]=2)[NH:7][CH:6]=1.C=O.[C:17](O)(=O)C>C(O)C>[ClH:1].[CH2:17]1[C:6]2[NH:7][C:8]3[C:13](=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=3)[C:5]=2[CH2:4][CH2:3][NH:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 712FormaldehydeHCID 160436Serotonin Hydrochloride

Product 1

HCID 220184982,3,4,9-tetrahydro-1H-beta-carbolin-6-ol hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(2-amino-ethyl)-1H-indol-5-ol hydrochloride (10.0 g) in 450 mL of absolute ethanol was added 1.6 g of paraformaldehyde and 5.4 mL of glacial acetic acid. The mixture was heated to reflux for 1.5 h then allowed to cool to rt. The white precipitate so formed was collected by filtration and dried under vacuum to yield 5.9 g of 2,3,4,9-tetrahydro-1H-β-carbolin-6-ol hydrochloride.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 h
  3. customThe white precipitate so formed
  4. filtrationwas collected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-94519c87f60641e69754c5d68bb615e7
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Linked notes

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