5-(Cyclohexyloxy)-3-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)-1H-indole → HCID 23288077, compound

HRID 367370Notes

Reaction equation

HRID 367370 reaction equation
[CH:1]1([O:7][C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][CH:12]=[C:11]3[C:17]2[CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH:22]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].CO>[CH:1]1([O:7][C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][CH:12]=[C:11]3[CH:17]2[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 232881505-(Cyclohexyloxy)-3-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)-1H-indole

Product 1

HCID 23288077HCID 23288077, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on carbon (10%, 31 mg) was added to a solution of 5-cyclohexyloxy-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (Example 4c, 48.4 mg, 0.16 mmol) in methanol (5 mL) and the mixture was stirred under an atmosphere of hydrogen for 8 h. Removal of the catalyst by filtration through celite and silica (20% 2M methanolic ammonia in dichloromethane) yielded 5-cyclohexyloxy-3-(1-methyl-4-piperidinyl)-1H-indole (quantitative, HRMS-FAB+ for C20H28N2O: calculated MH+: 313.22800; found MH+ : 313.23083).

Workup

  1. customRemoval of the catalyst
  2. filtrationby filtration through celite and silica (20% 2M methanolic ammonia in dichloromethane)

Sources & evidence

ORD record
ord-6379a16a64db4e44a249f130e3c6f6ac
Source dataset
uspto-grants-2000_10
Patent number
US06133287

Reaction notes

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