Phenylacetaldehyde → Ethyl 1-methyl-7-(2-phenylethylamino)-2-indolecarboxylate

HRID 565031Notes

Reaction equation

HRID 565031 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7]2.[C:17]1([CH2:23][CH:24]=O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH4-].N#CC#N.[Na+].[OH-].[Na+]>C(#N)C.C(O)(=O)C.C(O)(C)C>[CH3:11][N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[NH:1][CH2:24][CH2:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:7]=[C:8]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

8

Reactant 4

HCID 998PhenylacetaldehydeHCID 14798Sodium HydroxideHCID 21194578Ethyl 7-amino-1-methyl-2-indolecarboxylateHCID 131722252Sodium cyanogen borohydride

Product 1

HCID 21194741Ethyl 1-methyl-7-(2-phenylethylamino)-2-indolecarboxylateYield 30.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 3776IsopropanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.10 g (0.46 mmol) of ethyl 7-amino-1-methyl-2-indolecarboxylate, 0.12 g (0.50 mmol) of phenylacetaldehyde as 50% isopropanol solution, 0.043 g (0.69 mmol) of sodium cyanogen borohydride and 0.1 ml of acetic acid in 5 ml of acetonitrile was stirred at room temperature for 15 minutes. Thereafter 0.2 ml of acetic acid was added to the reaction mixture. The resulting mixture was allowed to stand at room temperature for 15 hours. After 1N sodium hydroxide solution was added to the reaction mixture, the mixture was extracted three times with diethyl ether. The combined extracts were then washed with 1N potassium hydroxide solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give 0.045 g (30.5%) of ethyl 1-methyl-7-(2-phenylethylamino)-2-indolecarboxylate.

Workup

  1. waitto stand at room temperature for 15 hours
  2. extractionthe mixture was extracted three times with diethyl ether
  3. washThe combined extracts were then washed with 1N potassium hydroxide solution
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ecdde33ada3045b6a0b223c2d05349c9
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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