Potassium Bicarbonate → HCID 86758640, compound

HRID 2297510Notes

Reaction equation

HRID 2297510 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([CH2:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[N:17])[CH:14]=3)[NH:9][CH:8]=2)[CH2:2]1.[C:18](=[O:21])([O-])[OH:19].[K+]>CC(=O)CC>[C:16]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:6][CH:3]1[CH2:4][CH2:5][N:1]([CH2:3][CH2:2][NH:1][C:18](=[O:21])[O:19][C:7]([CH3:15])([CH3:8])[CH3:6])[CH2:2]1)#[N:17]

Participants

4

Reactant 2

HCID 516893Potassium BicarbonateHCID 15511271HCID 15511271, compound

Product 1

HCID 86758640HCID 86758640, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

Under an inert atmosphere, 47.3 mmol (10 g) of 3-[(3-pyrrolidinyl)methyl]-1H-indole-5-carbonitrile, 47.3 mmol (9.95 g) of the product described in Preparation B and 1.55 ml of 2-butanone are mixed together and then 47.3 mmol (4.45 g) of potassium hydrogen carbonate are added. The mixture is stirred at 80° C. for 2 hours. After hydrolysis and separating off, the organic phase is washed with saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated. Purification is carried out by chromatography on silica, using a mixture of dichloromethane/methanol/ammonia 97/3/0.3 as eluant, to yield the expected product.

Workup

  1. additionare mixed together
  2. customAfter hydrolysis
  3. customseparating off
  4. washthe organic phase is washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification
  9. additiona mixture of dichloromethane/methanol/ammonia 97/3/0.3 as eluant

Sources & evidence

ORD record
ord-b68c33990ac444e0ba0375e3e5294554
Source dataset
uspto-grants-2002_12
Patent number
US06492366B1

Reaction notes

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