Water → HCID 677772, compound

HRID 1245846Notes

Reaction equation

HRID 1245846 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[OH:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+].O>CC(N(C)C)=O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:14]2[CH2:15][CH2:16][CH:11]([OH:10])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 79341Piperidin-4-ol

Product 1

HCID 677772HCID 677772, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

4-Bromobenzylbromide (3 g) was stirred with 4-hydroxypiperidine (1.21 g) and potassium carbonate (1.99 g) in dimethylacetamide (15 ml) at 50° C. for 3 h. The reaction mixture was then allowed to cool, poured into water (80 ml) and extracted with ethyl acetate (3×50 ml). The combined extracts were washed with water, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography, eluting with a gradient of 0–3% methanol in dichloromethane, to afford the product as a viscous, colourless oil (2.02 g).

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. washThe combined extracts were washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography
  8. washeluting with a gradient of 0–3% methanol in dichloromethane

Sources & evidence

ORD record
ord-f24dfaffb4314fe29a5a2681da1ef97a
Source dataset
uspto-grants-2006_10
Patent number
US07125896B2

Reaction notes

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