Piperidine → 3-(4-Methoxyphenylsulfanyl)-4-phenylbutyric acid

HRID 1107113Notes

Reaction equation

HRID 1107113 reaction equation
[C:1]1([CH2:7][CH:8]=[CH:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([SH:21])=[CH:17][CH:16]=1.N1CCCCC1>>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][CH:8]([CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:9][C:10]([OH:12])=[O:11])=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 8082PiperidineHCID 127654-MethoxybenzenethiolHCID 534018584-Phenyl-2-butenoic acid

Product 1

HCID 106381083-(4-Methoxyphenylsulfanyl)-4-phenylbutyric acidYield 82%

Conditions

Temperature
110 °C

Procedure

A mixture of 2 g (12.53 mmol) of 4-phenylbut-2-enoic acid, 1.8 mL (14.8 mmol) of 4-methoxybenzenethiol, and 0.4 mL (3.7 mmol) of piperidine is heated at 110° C. in a bomb for 18 hours. The reaction is partitioned between ethyl ether and 1N HCl. The organic layer is dried over anhydrous MgSO4 and concentrated in vacuo. Purification by flash silica gel chromatography affords 3.07 g (82%) of 3-(4-methoxyphenylsulfanyl)-4-phenylbutyric acid as a white crystalline solid.

Workup

  1. customThe reaction is partitioned between ethyl ether and 1N HCl
  2. dry with materialThe organic layer is dried over anhydrous MgSO4
  3. concentrationconcentrated in vacuo
  4. customPurification by flash silica gel chromatography

Sources & evidence

ORD record
ord-46b1720d905f4b3b9480bf6bc7369970
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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