Hydrochloric Acid → 9-methyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]-indole mono hydrochloride

HRID 1368104Notes

Reaction equation

HRID 1368104 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]([CH3:24])[C:13]=2[CH2:12]1)=O)C1C=CC=CC=1.[ClH:25]>CO.CCOC(C)=O.[Pd]>[ClH:25].[CH3:24][N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21]2[CH2:22][CH2:23][NH:11][CH2:12][C:13]1=2

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 120692932-benzyloxycarbonyl-9-methyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole

Product 1

HCID 224011859-methyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]-indole mono hydrochlorideYield 92%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-benzyloxycarbonyl-9-methyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole (5.17 g, 16.2 mmole) in methanol (100 mL), EtOAc (25 ml) and HCl (17 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 (3.19 g, 92%) as a white solid: MS (ES) m/e 187 (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-b2df522d25c24c6aaede10b7c7ccd297
Source dataset
uspto-grants-2003_06
Patent number
US06573272B1

Reaction notes

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