Thionyl Chloride → HCID 22628411, compound

HRID 278448Notes

Reaction equation

HRID 278448 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]([CH:13]=1)=[C:8]([CH2:11]O)[O:9][CH:10]=2.O=S(Cl)Cl.[CH3:18][C:19]1[CH:32]=[CH:31][C:22]([CH2:23][C:24]2([OH:30])[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:21][CH:20]=1>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:7]=[C:8]([CH2:11][N:27]3[CH2:28][CH2:29][C:24]([CH2:23][C:22]4[CH:21]=[CH:20][C:19]([CH3:18])=[CH:32][CH:31]=4)([OH:30])[CH2:25][CH2:26]3)[O:9][C:10]=2[CH:13]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 105362424-(4-Methylbenzyl)-piperidin-4-olHCID 56998706HCID 56998706, compound

Product 1

HCID 22628411HCID 22628411, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 6-methoxy-2-benzofuranmethanol (89 mg, 0.5 mmol) in dioxan (3 ml) at room temperature was added dropwise SOCl2 (0.11 ml, 1.5 mmol). After 1.5 hr, the reaction mixture was concentrated at room temperature under high vacuum. The residue was dissolved in dioxan (3 ml) and treated with 4-(4-methyl-benzyl)-piperidin-4-ol (225 mg, 1.1 mmol). After stirring 17 hr at room temperature, the solvent was evaporated. The residue was taken up in H2O (4 ml) and extracted with CH2Cl2 (6×4 ml). The combined organic phases were dried over Na2SO4, and concentrated. The residue was chromatographed over SiO2 (Merck 230-400 mesh) eluting with CH2Cl2—MeOH (19:1) to provide 1-(6-methoxy-benzofuran-2-ylmethyl)-4-(4-methyl-benzyl)-piperidin-4-ol (140 mg, 77%) as a yellow oil, MS:m/e=366.3 (M+H−+).

Workup

  1. concentrationthe reaction mixture was concentrated at room temperature under high vacuum
  2. dissolutionThe residue was dissolved in dioxan (3 ml)
  3. customthe solvent was evaporated
  4. extractionextracted with CH2Cl2 (6×4 ml)
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was chromatographed over SiO2 (Merck 230-400 mesh)
  8. washeluting with CH2Cl2—MeOH (19:1)

Sources & evidence

ORD record
ord-ca0919bcd9b04c229a84137c30974293
Source dataset
uspto-grants-2002_03
Patent number
US06359138B1

Reaction notes

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