Piperidine → 2-[1-(4-Phenoxyphenylthio)-cyclopent-1-yl]-acetic acid

HRID 1584390Notes

Reaction equation

HRID 1584390 reaction equation
[C:1]1(=[CH:6][C:7]([OH:9])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[O:10]([C:17]1[CH:22]=[CH:21][C:20]([SH:23])=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N1CCCCC1>C(OCC)(=O)C>[O:10]([C:17]1[CH:22]=[CH:21][C:20]([S:23][C:1]2([CH2:6][C:7]([OH:9])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 2974532-Cyclopentylideneacetic acidHCID 27603544-Phenoxythiophenol

Product 1

HCID 212241652-[1-(4-Phenoxyphenylthio)-cyclopent-1-yl]-acetic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of cyclopentylideneacetic acid (2 mmol) and p-(phenoxy)-thiophenol (2 mmol) was heated at 110° C. under nitrogen in the presence of piperidine (100 μL) for 24 hours. The residue was dissolved in ethyl acetate and washed with dilute hydrochloric acid. The organic layer was separated, dried and evaporated under reduced pressure to give crude 2-[-(4-phenoxyphenylthio)-cyclopent-1-yl]-acetic acid, which can be used in the next reaction without further purification.

Workup

  1. washwashed with dilute hydrochloric acid
  2. customThe organic layer was separated
  3. customdried
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0ea6accb447b4a57821c0acca957835a
Source dataset
uspto-grants-1999_08
Patent number
US05932595

Reaction notes

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