Acetic Acid → HCID 21467586, compound

HRID 1939394Notes

Reaction equation

HRID 1939394 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][C:8]2([Cl:18])C=O)=[CH:4][CH:3]=1.N1CCCC[CH2:22]1.C(O)(=O)C.[C:31]([O:39][CH2:40][CH3:41])(=[O:38])[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]>C(O)C>[CH2:40]([O:39][C:31]([C:32](=[CH:22][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:20][CH:19]=2)[C:8]=1[Cl:18])[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:38])[CH3:41]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 21467564HCID 21467564, compound

Product 1

HCID 21467586HCID 21467586, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 500 mg of 1-(4-Chlorobenzyl)-2-chloroindole-carbaldehyde, dissolved in 15 ml of a solvent which consisted of 5% piperidine and 2% acetic acid in absolute ethanol, was added 0.28 ml of diethyl malonate. After stirring for 3 days the solvent was removed by evaporation, and the product dissolved in 25 ml of ether plus 25 ml of 1N HCl. The organic phase was separated, and washed with 25 ml 1N HCl, 25 ml water, 25 ml of saturated NaHCO3 solution, dried (MgSO4) and evaporated to give an oil. Purification by column chromatography (methylene chloride on silica 60) gave (14a) as an oil which slowly crystallized. Yield 210 mg. M.p. 98°-99° C. (sample recryst. from EtOH/water).

Workup

  1. customwas removed by evaporation
  2. dissolutionthe product dissolved in 25 ml of ether
  3. customThe organic phase was separated
  4. washwashed with 25 ml 1N HCl, 25 ml water, 25 ml of saturated NaHCO3 solution
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give an oil
  8. customPurification by column chromatography (methylene chloride on silica 60)

Sources & evidence

ORD record
ord-26b7d99e3ef54d10a1ddada0ee282982
Source dataset
uspto-grants-1997_12
Patent number
US05696148

Reaction notes

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