Hydrochloric Acid → 9-Benzyl-2,3,4,9-tetrahydro-1H-beta-carboline

HRID 1681150Notes

Reaction equation

HRID 1681150 reaction equation
C([CH:4]1[C:16]2[N:15]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH2:7][CH2:6][NH:5]1)(=O)C.Cl>[OH-].[Na+].CO.O.C(OCC)C>[CH2:17]([N:15]1[C:16]2[CH2:4][NH:5][CH2:6][CH2:7][C:8]=2[C:9]2[C:14]1=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 54345929Acetyl 9-benzyl-1,2,3,4-tetrahydro-beta-carboline

Product 1

HCID 5986499-Benzyl-2,3,4,9-tetrahydro-1H-beta-carboline

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

A portion of the Orude -acetyl 9-benzyl-1,2,3,4-tetrahydro-β-carboline (1.7 g) was heated at reflux for 4.5 hours in 2 N NaOH (50 mL) in methanol:water 2:3, v/v). The methanol was removed by evaporation under vacuum, and the crude 9-benzyl-1,2,3,4-tetrahydro-β-carboline free base was extracted into chloroform. This extract was dried over anhydrous MgSO4, filtered, and the filtrate evaporated under vacuum. The hydrochloride salt was prepared by passing dry HCl through a solution of the crude free base in diethyl ether. The resulting precipitate was filtered and recrystallized from acetonitrile to yield pure 9-benzyl-1,2,3,4-tetrahydro-β-carboline.

Workup

  1. customThe methanol was removed by evaporation under vacuum
  2. extractionthe crude 9-benzyl-1,2,3,4-tetrahydro-β-carboline free base was extracted into chloroform
  3. dry with materialThis extract was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customthe filtrate evaporated under vacuum
  6. filtrationThe resulting precipitate was filtered
  7. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-687def125c664a63bf7e6a7d5e5521ab
Source dataset
uspto-grants-1992_12
Patent number
US05169852

Reaction notes

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