Piperidine → 3-(3,4-Dimethoxyphenylsulfanyl)-4-phenylbutanoic acid

HRID 1107141Notes

Reaction equation

HRID 1107141 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:16]=[C:17]([SH:23])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22].N1CCCCC1>>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([S:23][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:18]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

4

Reactant 3

HCID 8082PiperidineHCID 1365393,4-Dimethoxybenzene-1-thiolHCID 534018584-Phenyl-2-butenoic acid

Product 1

HCID 187901233-(3,4-Dimethoxyphenylsulfanyl)-4-phenylbutanoic acid

Conditions

Temperature
110 °C

Procedure

A mixture of 4-phenylbut-2-enoic acid (2 g, 12.33 mmol) prepared as in Example 6, Step B, 3,4-dimethoxybenzenethiol (2.1 mL, 14.79 mmol, 1.2 eq), and piperidine (0.4 mL (3.7 mmol, 0.3 eq) is heated at 110° C. in a bomb for 18 hours. The reaction is partitioned between ethyl ether and 1 N HCl. The organic layer is dried over anhydrous MgSO4 and concentrated in vacuo. The product is purified by flash silica gel chromatography to afford 3-(3,4-dimethoxyphenylsulfanyl)-4-phenylbutanoic acid as a yellow oil. (4.1 g, 100%): 1H-NMR (300 MHz, CDCl3) δ (TMS) 2.54(d, 0.5×2H), 2.56(d, 0.5×2H), 2.83(d, 0.5×2H), 2.98(d, 0.5×2H), 3.56(m, 1H), 3.85(s, 3H), 3.88(s, 3H), 6.8(d, 1H), 6.97(d, 1H), 7.05(d, 0.5×1H), 7.09(d, 0.5×1H), 7.15-7.32(m, 5H).

Workup

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

Sources & evidence

ORD record
ord-31aae315e79c4871983d26c3a82d4827
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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