Piperidine → HCID 16640441, compound

HRID 236791Notes

Reaction equation

HRID 236791 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10](O)=O)=[CH:4][CH:3]=1.O=S(Cl)Cl.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[S:8][C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:10]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 8082PiperidineHCID 24386Thionyl ChlorideHCID 16640368HCID 16640368, compound

Product 1

HCID 16640441HCID 16640441, compound

Procedure

20 g (72 mmole) of α-(4-chlorophenylthio)-phenylacetic acid and 20 milliliters (280 mmole) of SOCl2 are refluxed for 3 hours. After the excess SOCl2 has been removed, the crude acid chloride is dissolved in 100 milliliters of dioxan and, with stirring the cooling, 21.2 milliliters (290 mmole) of piperidine are added dropwise. After dilution in water, the mixture is extracted with CH2Cl2. By evaporating the organic phase dried over Na2SO4, 22.6 g (91% theory) of the piperidinium salt of α-(4-chlorophenylthio)-phenylacetic acid are obtained: colourless rods, mp 125°-126° (benzene/petroleum ether).

Workup

  1. customAfter the excess SOCl2 has been removed
  2. dissolutionthe crude acid chloride is dissolved in 100 milliliters of dioxan
  3. additionare added dropwise
  4. extractionAfter dilution in water, the mixture is extracted with CH2Cl2
  5. customBy evaporating the organic phase
  6. dry with materialdried over Na2SO4, 22.6 g (91% theory) of the piperidinium salt of α-(4-chlorophenylthio)-phenylacetic acid
  7. customare obtained

Sources & evidence

ORD record
ord-269be177b982407f9685128b99a24caf
Source dataset
uspto-grants-1979_06
Patent number
US04157399

Reaction notes

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