Potassium Carbonate → HCID 23498835, compound

HRID 1836142Notes

Reaction equation

HRID 1836142 reaction equation
[CH:1]([C:3]1[NH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[CH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:27])[CH2:22][O:23]C(=O)C)[CH2:17][CH2:16]1)=[O:2].C(=O)([O-])[O-].[K+].[K+].CO.O>ClCCl.CO>[OH:23][CH2:22][C:21]([N:18]1[CH2:17][CH2:16][N:15]([CH2:14][CH2:13][CH2:12][C:11]2[C:10]3[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=3[NH:4][C:3]=2[CH:1]=[O:2])[CH2:20][CH2:19]1)=[O:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 22242641Methanol--water (1/1)HCID 86588563acetic acid 2-{4-[3-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-piperazin-1-yl}-2-oxo-ethyl ester

Product 1

HCID 23498835HCID 23498835, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Each fraction of acetic acid 2-{4-[3-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-piperazin-1-yl}-2-oxo-ethyl ester was treated separately with potassium carbonate (3.0 eq.) in 6 ml of (methanol/ water 4/1). The two reactions were stirred at room temperature for overnight. Thin layer chromatography (dichloromethane: methanol 15:1) for both reactions showed the same spot and also LCMS showed that they have the same molecular weight. The two reactions were combined and the solvent was evaporated. The formed solid was washed with 30 ml of (dichloromethane/methanol 10/1) three times and sonicated. The liquid was collected and concentrated to give 268 mg of 3-{3-[4-(2-hydroxyacetyl)piperazin-1-yl]-propyl}-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde.

Workup

  1. customthe solvent was evaporated
  2. washThe formed solid was washed with 30 ml of (dichloromethane/methanol 10/1) three times
  3. customsonicated
  4. customThe liquid was collected
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3ac57756a19544f3b35f9fb782d83361
Source dataset
uspto-grants-2004_08
Patent number
US06777417B2

Reaction notes

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