1-Bromo-3-chloropropane → HCID 14526712, compound

HRID 1453786Notes

Reaction equation

HRID 1453786 reaction equation
[H-].[Na+].[NH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9].Br[CH2:11][CH2:12][CH2:13][Cl:14]>C1COCC1>[Cl:14][CH2:13][CH2:12][CH2:11][N:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 126652-PiperidoneHCID 24758Sodium hydride

Product 1

HCID 14526712HCID 14526712, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% suspension in oil, 26 mg, 0.65 mmol) was added to a solution of 2-piperidone (54 mg, 0.54 mmol) in dry THF (2 mL) under argon atmosphere. After 15 minutes stirring at rt the reaction mixture was cooled to 0° C. over 15 minutes. A solution of 1-bromo-3-chloropropane (160 μL, 1.62 mmol) was added dropwise to the cold mixture and stirring was continued overnight at rt. The mixture was partitioned between water and ethyl acetate, the organic layer dried over sodium sulphate, filtered and evaporated to dryness. Purification of the residue on silica gel column chromatography, eluting with a stepwise gradient of 60-80% ethyl acetate in n-heptane, afforded 1-(3-chloropropyl)piperidin-2-one (33 mg, 35%).

Workup

  1. temperaturewas cooled to 0° C. over 15 minutes
  2. stirringstirring
  3. waitwas continued overnight at rt
  4. customThe mixture was partitioned between water and ethyl acetate
  5. dry with materialthe organic layer dried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customPurification of the residue on silica gel column chromatography
  9. washeluting with a stepwise gradient of 60-80% ethyl acetate in n-heptane

Sources & evidence

ORD record
ord-46bb72aed16842dc80493dc836afd794
Source dataset
uspto-grants-2009_01
Patent number
US07476682B2

Reaction notes

Loading…