1-benzyl-1H-indole-3-carbaldehyde → HCID 10204285, compound

HRID 2415127Notes

Reaction equation

HRID 2415127 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([NH:15][CH2:16][CH2:17][CH2:18][NH2:19])[CH:6]=1.C[O-].[Na+].[CH2:23]([N:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]([CH:39]=O)=[CH:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[CH2:23]([N:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]([CH2:39][NH:19][CH2:18][CH2:17][CH2:16][NH:15][C:7]2[CH:6]=[C:5]([O:4][CH3:3])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)=[CH:31]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 2621041-benzyl-1H-indole-3-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 10942334Sodium MethoxideHCID 22640745HCID 22640745, compound

Product 1

HCID 10204285HCID 10204285, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent3×

Procedure

A solution of N′-(4-methoxyquinolin-2-yl)propane-1,3-diamine dihydrochloride (200 mg, 0.66 mmol) [4a] in methanol (50 ml) was treated with glacial acetic acid (20 drops) and sodium methoxide (95%, 71 mg, 1.31 mmol) followed by a solution of 1-benzyl-3-indole carboxaldehyde (155 mg, 0.66 mmol) in methanol (5.0 ml). The reaction stirred at ambient temperature for 24 hours then was treated with a solution of sodium cyanoborohydride (83 mg, 1.31 mmol) in methanol (2.0 ml). The reaction stirred at ambient temperature for 24 hours. The solution was evaporated under reduced pressure to a residue that was taken into a mixture of saturated aqueous sodium chloride (20 ml) and 10% sodium hydroxide solution (20 ml). It was extracted in ethyl acetate and the extracts were dried (sodium sulfate) then concentrated to an oil. Column chromatography on silica (95/5 dichloromethane/methanolic ammonia) gave N-(1-benzyl-1H-indol-3-ylmethyl)-N′-(4-methoxyquinolin-2-yl)propane-1,3-diamine (126 mg, 84%) as a white solid. [M+H]+ 451.

Workup

  1. stirringThe reaction stirred at ambient temperature for 24 hours
  2. customThe solution was evaporated under reduced pressure to a residue that
  3. additionwas taken into a mixture of saturated aqueous sodium chloride (20 ml) and 10% sodium hydroxide solution (20 ml)
  4. extractionIt was extracted in ethyl acetate
  5. dry with materialthe extracts were dried (sodium sulfate)
  6. concentrationthen concentrated to an oil

Sources & evidence

ORD record
ord-e412cdcb683e433ba12308c38f8ae7cc
Source dataset
uspto-grants-2004_11
Patent number
US06818655B2

Reaction notes

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