Potassium Hydroxide → [3-(6-Methoxy-1H-indol-4-yl)-3-phenyl-propyl]-methyl-amine

HRID 268819Notes

Reaction equation

HRID 268819 reaction equation
[CH3:1][NH2:2].Cl.[OH-].[K+].[CH3:6][O:7][C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[CH:13][NH:14]2)=[C:10]([CH:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:18][CH:19]=O)[CH:9]=1>CO>[CH3:6][O:7][C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[CH:13][NH:14]2)=[C:10]([CH:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:18][CH2:19][NH:2][CH3:1])[CH:9]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 6364545Methylamine hydrochlorideHCID 598319133-(6-Methoxy-1H-Indol-4-yl)-3-phenyl-propionaldehyde

Product 1

HCID 25261734[3-(6-Methoxy-1H-indol-4-yl)-3-phenyl-propyl]-methyl-amineYield 13%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a mixture of MeNH2.HCl (0.60 g, 9 mmol) and KOH (0.1 g, 1.8 mmol) in MeOH (5 ml) was added a solution of 3-(6-Methoxy-1H-Indol-4-yl)-3-phenyl-propionaldeyde CXVIII (0.25 g, 0.89 mmol) in MeOH (6 ml) at RT. The resulting mixture was stirred at room temperature for 5 minutes and NaCNBH4 (21 mg, 0.33 mmol) was added. The reaction mixture was stirred for 45 minutes at room temperature and then quenched with HCl (1M, 50 ml). The resulting mixture was extracted with Et2O (25 ml), and the aqueous layer was basified until pH>12 by addition of a saturated solution of NaOH (50 ml). The aqueous layer was extracted with Et2O (35 ml). The combined organic layers were dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (DCM/MeOH/NH4OH) to afford [3-(6-Methoxy-1H-indol-4-yl)-3-phenyl-propyl]-methyl-amine compound CXIX (33 mg, 13% yield). MS (M+H)=295.

Workup

  1. additionNaCNBH4 (21 mg, 0.33 mmol) was added
  2. stirringThe reaction mixture was stirred for 45 minutes at room temperature
  3. customquenched with HCl (1M, 50 ml)
  4. extractionThe resulting mixture was extracted with Et2O (25 ml)
  5. additionthe aqueous layer was basified until pH>12 by addition of a saturated solution of NaOH (50 ml)
  6. extractionThe aqueous layer was extracted with Et2O (35 ml)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified via flash chromatography (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-ae6bc89ed5074fd49e622cff8d370454
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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