Water → HCID 11268439, compound

HRID 1678152Notes

Reaction equation

HRID 1678152 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH:20]=[O:21])=[C:12]2Cl)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.O>O1CCOCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH:20]=[O:21])=[C:12]2[N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4837PiperazineHCID 860359201-(4-tert-butylphenyl)-2-chloro-1H-indole-3-carboxaldehyde

Product 1

HCID 11268439HCID 11268439, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1-(4-tert-butylphenyl)-2-chloro-1H-indole-3-carboxaldehyde (2.95 g, 9.46 mmol), piperazine (10.60 g, 123 mmol) in dioxane (50 mL) is heated overnight at 110° C. Water is added and the reaction mixture is extracted with ethyl acetate. The combined ethyl acetate layers are washed with brine, dried and concentrated. The crude material is purified by chromatography eluting with dichloromethane-5% methanol. Fractions containing product are combined and concentrated to afford 1-(4-tert-butylphenyl)-2-piperazin-1-yl-1H-indole-3-carboxaldehyde (2.4 g, 70% yield) as a light cream solid. TLC (silica gel, dichloromethane-10% methanol) Rf=0.27; ESI/MS 362 (M+H), RT 3.27 min; NMR 10.14 (1H, s); 8.12 (1H, d, J=3Hz); 8.09 (2H, d); 7.68 (2H, d); 7.47 (2H, m); 6.91 (1H, d, J=6 Hz); 3.20 (4H, m); 2.53 (4H, m); 2.25 (1H, br s); 1.36 (9H, s).

Workup

  1. extractionthe reaction mixture is extracted with ethyl acetate
  2. washThe combined ethyl acetate layers are washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe crude material is purified by chromatography
  6. washeluting with dichloromethane-5% methanol
  7. additionFractions containing product
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-89085c87f0554ae48c9158da363d20ea
Source dataset
uspto-grants-2011_08
Patent number
US08008491B2

Reaction notes

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