Benzene, 1-bromo-4-(hexyloxy)- → 1-Benzyloxycarbonyl-4-(4-hexyloxyphenyl)-4-hydroxypiperidine

HRID 351543Notes

Reaction equation

HRID 351543 reaction equation
[Mg].[CH2:2]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][CH:10]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH2:16]([O:23][C:24]([N:26]1[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCCC1>[CH2:16]([O:23][C:24]([N:26]1[CH2:31][CH2:30][C:29]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH:10][CH:11]=2)([OH:32])[CH2:28][CH2:27]1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 520492Benzene, 1-bromo-4-(hexyloxy)-HCID 643496Benzyl 4-oxopiperidine-1-carboxylateHCID 5462224Magnesium

Product 1

HCID 227131741-Benzyloxycarbonyl-4-(4-hexyloxyphenyl)-4-hydroxypiperidineYield 47.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of magnesium turnings (0.48 g) in tetrahydrofuran (10 ml) was added dropwise a solution of 4-hexyloxybromobenzene (5 g) in tetrahydrofuran (70 ml) and stirred for 1 hour at ambient temperature. Then to the reaction mixture was added 1-benzyloxycarbonyl-4-piperidone (4.12 g) and stirred for 2 hours under ice-cooling. The reaction was quenched with saturated NH4Cl aq. and extracted with ethyl acetate. The organic layer was taken and dried over magnesium sulfate. The magnesium sulfate was filtered off, and filtrate was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with (hexane/ethyl acetate)=(3/1). The fractions containing the object compound were collected and evaporated under reduced pressure to give 1-benzyloxycarbonyl-4-(4-hexyloxyphenyl)-4-hydroxypiperidine (3.44 g).

Workup

  1. stirringstirred for 2 hours under ice-
  2. temperaturecooling
  3. customThe reaction was quenched with saturated NH4Cl aq.
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe magnesium sulfate was filtered off
  7. customfiltrate was evaporated under reduced pressure
  8. washeluted with (hexane/ethyl acetate)=(3/1)
  9. additionThe fractions containing the object compound
  10. customwere collected
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a464019cd42846e7abb2b9786be358dd
Source dataset
uspto-grants-2004_06
Patent number
US06743776B2

Reaction notes

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