Piperidine → HCID 19842210, compound

HRID 280535Notes

Reaction equation

HRID 280535 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH2:11][C:12]([OH:14])=O)[N:3]1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=1.C(N(CC)CC)C.C(OC(Cl)=O)C.[NH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>O1CCCC1>[N:35]1([C:12]([CH2:11][CH:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2](=[O:1])[N:3]2[C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=2)=[O:14])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 19842220[2-(5-Chloropyridin-2-yl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]acetic acid

Product 1

HCID 19842210HCID 19842210, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Oxo-2-(5-chloro-2-pyridyl)isoindoline-1-acetic acid (1 g) and triethylamine (0.8 g) were dissolved in 20 ml of dry tetrahydrofuran and, under ice-cooling with stirring, 0.39 g of ethoxycarbonyl chloride was added portionwise. The mixture was stirred for 3 minutes, 0.56 g of piperidine was added, and the whole mixture was stirred for an additional 30 minutes. The reaction mixture was poured into 500 ml of ice water, followed by extraction with ethyl acetate. The extract was washed with water and dried. The ethyl acetate was then distilled off and the residue was treated with ether. The resulting crystals thus obtained were collected by filtration and recrystallized from ethyl acetate to give 0.32 g of colorless crystals, melted at 165°-166° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 3 minutes
  3. stirringthe whole mixture was stirred for an additional 30 minutes
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. distillationThe ethyl acetate was then distilled off
  8. additionthe residue was treated with ether
  9. customThe resulting crystals thus obtained
  10. filtrationwere collected by filtration
  11. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4b5c12df79034871bd55a84966ecafe2
Source dataset
uspto-grants-1986_05
Patent number
US04590189

Reaction notes

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