Benzyl Bromide → HCID 54070323, compound

HRID 990096Notes

Reaction equation

HRID 990096 reaction equation
[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 18419728HCID 18419728, compound

Product 1

HCID 54070323HCID 54070323, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

N-Butoxycarbonyl-4-piperidinecarboxylic acid (4.6 g) was dissolved in dimethylformamide (20 ml) and placed under an atmosphere of nitrogen. Benzyl bromide (2.9 ml) and potassium carbonate (8.3 g) were added and heated at 60° C. for 3 h. The dimethylformamide was removed in vacuo and azeotroped with toluene (three times). The residue was dispersed between ethyl acetate and water and the aqueous phase was extracted with ethyl acetate (3×100 ml). The combined organic phases were washed with brine and dried (MgSO4). The solution was filtered, evaporated to dryness and the residue was purified by chromatography on silica gel (eluting with isohexane containing increasing concentrations amounts of ethyl acetate 5-30%) to give benzyl N-butoxycarbonylpiperidine-4-carboxylate as a clear oil (7.68 g).

Workup

  1. customThe dimethylformamide was removed in vacuo
  2. customazeotroped with toluene (three times)
  3. additionThe residue was dispersed between ethyl acetate and water
  4. extractionthe aqueous phase was extracted with ethyl acetate (3×100 ml)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationThe solution was filtered
  8. customevaporated to dryness
  9. customthe residue was purified by chromatography on silica gel (eluting with isohexane containing increasing concentrations amounts of ethyl acetate 5-30%)

Sources & evidence

ORD record
ord-5a927e5a818d4693a9a42241399edd49
Source dataset
uspto-grants-2002_10
Patent number
US06458830B1

Reaction notes

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