Hydrochloric Acid → HCID 9817950, compound

HRID 635385Notes

Reaction equation

HRID 635385 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17]CC3C=CC=CC=3)=[CH:14][CH:15]=2)[C:10]([CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[C:10]([CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10883747HCID 10883747, compound

Product 1

HCID 9817950HCID 9817950, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5-benzyloxy-3-(2-dimethylamino-ethyl)-1H-indole-1-carboxylic acid tert-butyl ester (303 mg, 0.77 mmol) and 4N hydrochloric acid (192 ml, 0.77 mmol) in ethanol (10 ml) was hydrogenated over 10% palladium on carbon (100 mg) at 40 psi for 4 hours. The catalyst was removed by filtration. The filtrate was evaporated and the residue was partitioned between aqueous sodium hydrogen carbonate and dichloromethane. The aqueous was further extracted with dichloromethane (×2). The combined extracts were dried (K2CO3), filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with dichloromethane/methanol/aqueous ammonia (60:8:1) to give the title compound (117 mg, 50%) as a colourless solid. δH (360 MHz, CDCl3) 1.64 (9H, s), 2.45 (6H, s), 2.73-2.80 (2H, m), 2.88-2.93 (2H, m), 6.82-6.85 (1H, m), 6.96 (1H, br s), 7.33 (1H, br s), 7.92 (1H, m). m/z (CI+) 305 [MH]+. Found: C, 64.07; H, 8.07; N, 8.71. C17H24N2O3. 0.8 H2O requires C, 64.01; H, 8.15; N, 8.78%.

Workup

  1. customThe catalyst was removed by filtration
  2. customThe filtrate was evaporated
  3. customthe residue was partitioned between aqueous sodium hydrogen carbonate and dichloromethane
  4. extractionThe aqueous was further extracted with dichloromethane (×2)
  5. dry with materialThe combined extracts were dried (K2CO3)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography on silica gel
  9. washeluting with dichloromethane/methanol/aqueous ammonia (60:8:1)

Sources & evidence

ORD record
ord-0a7dd0d2e37a4163abc6e4fba948fc11
Source dataset
uspto-grants-2001_02
Patent number
US06187805B1

Reaction notes

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