Triethylamine → 4-(Acetylthio)-1-[(E)-4-(trifluoromethoxy)cinnamoyl]-piperidine

HRID 381426Notes

Reaction equation

HRID 381426 reaction equation
Cl.[C:2]([S:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)(=[O:4])[CH3:3].C(N(CC)CC)C.[F:19][C:20]([F:34])([F:33])[O:21][C:22]1[CH:32]=[CH:31][C:25](/[CH:26]=[CH:27]/[C:28](Cl)=[O:29])=[CH:24][CH:23]=1>ClCCl>[C:2]([S:5][CH:6]1[CH2:11][CH2:10][N:9]([C:28](=[O:29])/[CH:27]=[CH:26]/[C:25]2[CH:24]=[CH:23][C:22]([O:21][C:20]([F:33])([F:34])[F:19])=[CH:32][CH:31]=2)[CH2:8][CH2:7]1)(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5709512(E)-3-[4-(trifluoromethoxy)phenyl]prop-2-enoyl chlorideHCID 183632904-(Acetylthio)piperidine hydrochloride

Product 1

HCID 183632734-(Acetylthio)-1-[(E)-4-(trifluoromethoxy)cinnamoyl]-piperidineYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 17 ml of dichloromethane were suspended 1.28 g (6.53 mmol) of 4-(acetylthio)piperidine hydrochloride, and 2.27 ml (16.3 mmol) of triethylamine were added dropwise to the suspension with stirring under ice-cooling. Then, a solution in which 1.80 g (7.18 mmol) of (E)-4-(trifluoromethoxy)cinnamoyl chloride were dissolved in 6 ml of dichloromethane was added dropwise to the reaction mixture, followed by stirring of the mixture at the same temperature for 1 hour. The reaction mixture was subjected to silica gel column chromatography and eluted with a mixed solvent of hexane-ethyl acetate (2:1 to 1:1) to obtain 2.32 g (yield: 95%) of the desired compound as a slightly yellow solid.

Workup

  1. additionwere added dropwise to the suspension
  2. temperaturecooling
  3. additionwas added dropwise to the reaction mixture
  4. stirringby stirring of the mixture at the same temperature for 1 hour
  5. washeluted with a mixed solvent of hexane-ethyl acetate (2:1 to 1:1)

Sources & evidence

ORD record
ord-dd0d8d33777e4922a6180c4a6849328e
Source dataset
uspto-grants-2001_10
Patent number
US06306880B1

Reaction notes

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