Hydrochloric Acid → HCID 9796627, compound

HRID 635384Notes

Reaction equation

HRID 635384 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19])[CH:13]=[C:12]2[CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])C1C=CC=CC=1.Cl>C(O)C.[Pd]>[CH3:30][N:28]([CH3:29])[CH2:27][CH2:26][C:12]1[C:11]2[C:15](=[CH:16][CH:17]=[C:9]([OH:8])[CH:10]=2)[N:14]([C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:19])[CH:13]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11101390HCID 11101390, compound

Product 1

HCID 9796627HCID 9796627, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of [5-benzyloxy-3-(2-dimethylamino-ethyl)-1H-indol-1yl]phenylmethanone (300 mg, 0.75 mmol) and 4N hydrochloric acid (190 ml, 0.76 mmol) in ethanol (10 ml) was hydrogenated over 10% palladium on carbon (100 mg) at 35 psi for 3 hours. The catalyst was removed by filtration. The filtrate was evaporated, and the residue was partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate. 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/aqueotus ammonia (80:8:1) to give the title compound (120 mg, 52%), as a colourless solid; mp 154°-156° C. δH (360 MHz, CDCl3) 2.40 (6H, s), 2.70-2.75 (2H, m), 2.83-2.88 (2H, m), 6.86-6.90 (2H, m), 7.04 (1H, s), 7.49-7.61 (3H, m), 7.68-7.71 (2H, m), 8.17 (0.5H, s), 8.20 (0.5H, s). m/z (CI+) 309 [MH]+. Found: C, 73.22; H, 6.48; N, 8.74. C19H20N2O2.0.2 H2O requires C, 73.15; H, 6.59; N, 8.98%.

Workup

  1. customThe catalyst was removed by filtration
  2. customThe filtrate was evaporated
  3. customthe residue was partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate
  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/aqueotus ammonia (80:8:1)

Sources & evidence

ORD record
ord-090a2967f5be49de83975f1c1cea1abc
Source dataset
uspto-grants-2001_02
Patent number
US06187805B1

Reaction notes

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