Water → HCID 66615739, compound

HRID 1878794Notes

Reaction equation

HRID 1878794 reaction equation
Cl.[Cl:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[C:5]([CH3:16])[CH:4]=1.C(N(CC)CC)C.[CH:24]1([C:29](Cl)=[O:30])[CH2:28][CH:27]=[CH:26][CH2:25]1.O>ClCCl>[Cl:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH:8]2[CH2:9][CH2:10][N:11]([C:29]([CH:24]3[CH2:28][CH:27]=[CH:26][CH2:25]3)=[O:30])[CH2:12][CH2:13]2)=[C:5]([CH3:16])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13173314Cyclopent-3-ene-1-carbonyl chlorideHCID 56830768HCID 56830768, compound

Product 1

HCID 66615739HCID 66615739, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-(4-Chloro-2-methylphenoxy)piperidine hydrochloride (28.6 g) and triethylamine (45.5 mL) were stirred in dichloromethane (100 mL) and cyclopent-3-ene-1-carbonyl chloride (14.26 g) in dichloromethane (100 mL) was added dropwise. When addition was complete, the reaction mixture was stirred at room temperature for 2 h. Water (250 mL) was added to the reaction mixture and product was extracted with dichloromethane. The dichloromethane was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was filtered through a plug of silica eluting with diethyl ether to give the subtitle compound (29.5 g).

Workup

  1. additionWhen addition
  2. extractionwas extracted with dichloromethane
  3. washThe dichloromethane was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. filtrationThe crude product was filtered through a plug of silica eluting with diethyl ether

Sources & evidence

ORD record
ord-2419456e5fe14a3ca7c7f8e787c850d5
Source dataset
uspto-grants-2012_11
Patent number
US08314127B2

Reaction notes

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