Hydrochloric Acid → 9-{[4-(fluoro)phenyl]methyl}-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]-indole mono hydrochloride

HRID 1368109Notes

Reaction equation

HRID 1368109 reaction equation
C(OC([N:11]1[CH2:23][CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[C:13]=2[CH2:12]1)=O)C1C=CC=CC=1.[ClH:32]>CO.O1CCOCC1.[Pd]>[ClH:32].[F:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][N:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21]3[CH2:22][CH2:23][NH:11][CH2:12][C:13]2=3)=[CH:26][CH:27]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 120692962-benzyloxycarbonyl-9-{[4-(fluoro)phenyl]methyl}-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole

Product 1

HCID 865905139-{[4-(fluoro)phenyl]methyl}-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]-indole mono hydrochlorideYield 90%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-benzyloxycarbonyl-9-{[4-(fluoro)phenyl]methyl}-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole (5.28 g, 12.7 mmole) in methanol (50 mL), dioxane (50 mL) and HCl (19 mL, 1M in dioxane) at RT in a Parr hydrogenation flask was added 10% Pd/C (0.5 g). The reaction mixture was shaken under 45 psi of H2 for 6 hr. The suspension was filtered through celite®, and the filter pad was washed with methanol. The filtrate was concentrated on the rotavap, and the residue was dried under high vacuum to afford the titled compound (3.61 g, 90%) as a white solid: MS (ES) m/e 281 (M+H−HCl)+.

Workup

  1. filtrationThe suspension was filtered through celite®
  2. washthe filter pad was washed with methanol
  3. concentrationThe filtrate was concentrated on the rotavap
  4. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-4050c21630f840abb48765d1ddc6aa11
Source dataset
uspto-grants-2003_06
Patent number
US06573272B1

Reaction notes

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