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

HRID 6741

Reaction equation

HRID 6741 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[CH:18](O)[C:19]([F:22])([F:21])[F:20])C.C(O)(=O)C>C(O)C>[ClH:1].[F:20][C:19]([F:22])([F:21])[CH:18]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 9897Ethanol, 1-ethoxy-2,2,2-trifluoro-HCID 160436Serotonin Hydrochloride

Product 1

HCID 220185001-trifluoromethyl-2,3,4,9-tetrahydro-1H-beta-carbolin-6-ol hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(2-amino-ethyl)-1H-indol-5-ol hydrochloride (0.5 g), trifluoroacetaldehyde ethyl hemiacetal (0.35 mL), acetic acid (0.32 mL) and ethanol (22.5 mL) was heated at reflux for 16 h. The solvent and excess reagents were evaporated to dryness under vacuum. The residue was washed with diethyl ether to afford 1-trifluoromethyl-2,3,4,9-tetrahydro-1H-β-carbolin-6-ol hydrochloride (0.5 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. customThe solvent and excess reagents were evaporated to dryness under vacuum
  4. washThe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-600460d8babf4f8aadae29babece78a3
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Linked notes

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