4-Chlorophenol → HCID 70051233, compound

HRID 1757142Notes

Reaction equation

HRID 1757142 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:14][C@H:13]3[N:15]([CH3:16])[C@H:10]([CH2:11][CH2:12]3)[C@@H:9]2[C:17]([O-:19])=[O:18])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[Cl:24][C:25]1[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=1.C(N(CC)CC)C>C(OCC)C.O1CCCC1>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([O:18][C:17]([C@@H:9]2[C@@H:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:14][C@H:13]3[N:15]([CH3:16])[C@@H:10]2[CH2:11][CH2:12]3)=[O:19])=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 46844-ChlorophenolHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 86748285HCID 86748285, compound

Product 1

HCID 70051233HCID 70051233, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (1R,2R,3S)-3-(4-fluorophenyl)tropane 2-carboxylate (1.4 g, 5 mmol) and thionyl chloride (5 ml) was refluxed for one hour and the reaction mixture was concentrated in vacuo. The remanescens was suspended in diethyl ether (20 ml) and a solution of 4-chlorophenol (0.64 g, 5 mmol) and triethyl amine (1.4 ml, 10 mmol) in diethyl ether (10 ml) was added at room temperature. The mixture was stirred at room temperature over night and tetrahydrofurane (30 ml) was added and the mixture was refluxed for three hours. The reaction was quenched by addition of water (50 ml) and was extracted with diethyl ether. The combined organic phase was washed with sodium hydroxide (1M) and three times with water. After drying and concentration in vacuo the crude product was subjected to column chromatography first with ethyl acetate and later with ethyl acetate and methanol (20%) as eluent yielding the title compound as white crystals, m.p. 64°-66° C.

Workup

  1. temperaturewas refluxed for one hour
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. temperaturethe mixture was refluxed for three hours
  4. customThe reaction was quenched by addition of water (50 ml)
  5. extractionwas extracted with diethyl ether
  6. washThe combined organic phase was washed with sodium hydroxide (1M) and three times with water
  7. customAfter drying
  8. concentrationconcentration in vacuo the crude product

Sources & evidence

ORD record
ord-bc680e4350bc41b1b143c05e195cd11e
Source dataset
uspto-grants-1995_08
Patent number
US05444070

Reaction notes

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