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

HRID 1368106Notes

Reaction equation

HRID 1368106 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]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)[C:13]=2[CH2:12]1)=O)C1C=CC=CC=1.[ClH:35]>CO.O1CCOCC1.[Pd]>[ClH:35].[F:34][C:31]([F:32])([F:33])[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 120692942-benzyloxycarbonyl-9-{[4-(trifluoromethyl)phenyl]methyl}-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole

Product 1

HCID 185199049-{[4-(Trifluoromethyl)phenyl]methyl}-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]-indole mono hydrochlorideYield 92%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-benzyloxycarbonyl-9-{[4-(trifluoromethyl)phenyl]methyl}-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole (8.73 g, 18.81 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 (6.33 g, 92%) as a white solid: MS (ES) m/e 331 (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-09fedb64e67842808f04ad95b6c8d04e
Source dataset
uspto-grants-2003_06
Patent number
US06573272B1

Reaction notes

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