Potassium sodium tartarate → HCID 9883089, compound

HRID 1720062Notes

Reaction equation

HRID 1720062 reaction equation
[NH2:1][C:2](=O)[C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:12]=2)[NH:7][CH:6]=1)=O.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1>[NH2:1][CH2:2][CH2:3][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:12]=2)[NH:7][CH:6]=1

Participants

4

Reactant 2

HCID 9855836Potassium sodium tartarateHCID 15342550HCID 15342550, compound

Product 1

HCID 9883089HCID 9883089, compoundYield 32.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of the 3-(2-amino-1,2-dioxoethyl)-5-(4-phenylbutyloxy)indole (0.4 g, 1.3 mmol) and LiAIH4 (0.32 g, 8.44 mmol) in dry THF (30 ml) was heated at reflux for 3 days under nitrogen. After allowing the reaction mixture to cool to room temperature, the excess LiAIH4 was decomposed by the addition of a saturated solution of sodium potassium tartrate (3 ml) at 0° C. The precipitated material was removed by filtration and the flitrate was dried (MgSO4). The solvent was removed under reduced pressure to afford an oily product. The oil was purified by column chromatography using a solvent system of CH2Cl2/MeOH (90:10) to provide 3-(2-aminoethyl)-5-(4-phenylbutyloxy)indole (32.8% yield) as an oil. The oil was taken up in anhydrous Et2O (5 ml) and added to a saturated ethereal solution of oxalic acid. The resultant oxalate salt was collected by filtration, washed with anhydrous Et2O (2×10 ml), and recrystallized from MeOH/Et2O to afford a tan solid; mp 130°-132° C. Analytically calculated formula C20H24N2O. (COOH)2.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 days under nitrogen
  3. customThe precipitated material was removed by filtration
  4. dry with materialthe flitrate was dried (MgSO4)
  5. customThe solvent was removed under reduced pressure
  6. customto afford an oily product
  7. customThe oil was purified by column chromatography

Sources & evidence

ORD record
ord-a88d8ca0702145909d574fbed5d37540
Source dataset
uspto-grants-1996_04
Patent number
US05504101

Reaction notes

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