Hydrochloric Acid → HCID 23383899, compound

HRID 1047360Notes

Reaction equation

HRID 1047360 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([Mg]Br)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([N:23]1[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>O1CCCC1.C(OCC)C>[CH2:16]([N:23]1[CH2:28][CH2:27][C:26]([C:11]2[CH:12]=[CH:13][C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:9][CH:10]=2)([OH:29])[CH2:25][CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 192201-Benzyl-4-piperidoneHCID 178419636HCID 178419636, compound

Product 1

HCID 23383899HCID 23383899, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A 0.5 M solution of 4-phenoxy-phenylmagnesium bromide in tetrahydrofuran (30 mL, 15 mmol) was introduced into a flame-dried flask placed under an argon atmosphere. A solution of 1-benzyl-4-piperidone (2.84 g, 15 mmol) in dry tetrahydrofuran (12 mL) was then added dropwise, while the temperature was maintained at less than 20° C. with an ice bath. After completion of the addition, the mixture was allowed to reach room temperature and further stirred for 2 hr. Ice was then added to the mixture, and 1 N HCl was added until the resulting precipitate was completely dissolved. The reaction was then diluted with diethyl ether (100 mL) and washed with water (50 mL). The aqueous layer was extracted with diethyl ether (2×50 mL), and the combined organic layers were sequentially washed with saturated aqueous sodium hydrogencarbonate (2×50 mL) and water (50 mL), dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by column chromatography on silica gel (dichloromethane and then diethyl ether). The desired product was then isolated as a colorless solid (1.74 g, 33% yield).

Workup

  1. temperaturewas maintained at less than 20° C. with an ice bath
  2. additionAfter completion of the addition
  3. customto reach room temperature
  4. additionwas added until the resulting precipitate
  5. dissolutionwas completely dissolved
  6. washwashed with water (50 mL)
  7. extractionThe aqueous layer was extracted with diethyl ether (2×50 mL)
  8. washthe combined organic layers were sequentially washed with saturated aqueous sodium hydrogencarbonate (2×50 mL) and water (50 mL)
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under vacuum
  12. customThe crude product was purified by column chromatography on silica gel (dichloromethane

Sources & evidence

ORD record
ord-8899656c6d584676ba100c56d4d1a90c
Source dataset
uspto-grants-2013_10
Patent number
US08569495B2

Reaction notes

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