Hydrochloric Acid → HCID 117987668, compound

HRID 2205962Notes

Reaction equation

HRID 2205962 reaction equation
[CH:1]1([N:6]2[CH:10]=[CH:9][CH:8]=[C:7]2[CH:11]=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(=O)[CH2:14][C:15]([OH:17])=[O:16].N1CCCCC1.Cl>N1C=CC=CC=1>[CH:1]1([N:6]2[CH:10]=[CH:9][CH:8]=[C:7]2/[CH:11]=[CH:14]/[C:15]([OH:17])=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 17604933HCID 17604933, compound

Product 1

HCID 117987668HCID 117987668, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1-cyclopentyl-1H-pyrrole-2-carbaldehyde (10.4 g), malonic acid (20.0 g) and piperidine (1.71 mL) in pyridine (64.0 mL) was refluxed overnight. The obtained reaction mixture was allowed to be cooled to room temperature, and then slowly poured into ice and 6N hydrochloric acid (300 mL). The mixture was extracted with dichloromethane, and the organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (6.74 g).

Workup

  1. customThe obtained reaction mixture
  2. extractionThe mixture was extracted with dichloromethane
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f8c16016207e48f5a0e32003b64a5ece
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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