2-(4-Fluorophenyl)acetic acid → 7-Methoxy-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 1790490Notes

Reaction equation

HRID 1790490 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][CH:10]2N2CCNCC2)=[CH:5][CH:4]=1.FC1C=CC(CC(O)=[O:28])=CC=1.S(Cl)(Cl)=O>C(Cl)Cl>[OH:28][CH:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2)[CH2:7][CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 98372-(4-Fluorophenyl)acetic acidHCID 24386Thionyl ChlorideHCID 14601169(7-Methoxytetralin-1-yl)piperazine

Product 1

HCID 122431977-Methoxy-1,2,3,4-tetrahydronaphthalen-1-olYield 129%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-Methoxy-1-(piperazin-1-yl)-1,2,3,4-tetrahydronaphthalene (0.6 g) was reacted in methylene chloride for 2 hr with an acid chloride prepared from 4-fluorophenylacetic acid (0.44 g) and thionyl chloride (0.21 ml) Then the liquid reaction mixture was partitioned between methylene chloride and water, extracted with methylene chloride, dried and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (toluene/acetone system) to give the title compound (0.56 g) as an oil. (280-5) 1-{4-[2-(4-Fluorophenyl)ethyl]piperdin-1-yl}-7-methoxy-1,2,3,4-tetrahydronaphthalene

Workup

  1. customthe liquid reaction mixture
  2. customwas partitioned between methylene chloride and water
  3. extractionextracted with methylene chloride
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (toluene/acetone system)

Sources & evidence

ORD record
ord-ad822638d79f4e5b8be7ef4382902fdb
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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