1,6-Dibromohexane → HCID 13289795, compound

HRID 1388339Notes

Reaction equation

HRID 1388339 reaction equation
[H-].[Na+].Br[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][Br:10].[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C:12]1=[O:17]>CN(C)C=O.O.CCCCCC>[Br:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C:12]1=[O:17]

Participants

7

Reactant 3

HCID 123681,6-DibromohexaneHCID 126652-PiperidoneHCID 24758Sodium hydride

Product 1

HCID 13289795HCID 13289795, compoundYield 18.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

Following the procedure of Example 1, sodium hydride (3.63 g of 50% dispersion in oil, 0.15 mole), 1,6-dibromohexane (23.07 ml, 0.15 mole) and 2-piperidone (7.5 g, 0.076 mole) were reacted in dimethylformamide. The filtered, concentrated reaction mixture was taken up in 200 ml of water and 200 ml of hexane. The hexane layer was separated and evaporated to an oil. The oil was chromatographed on silica gel using ethyl acetate as eluant and tlc monitoring. Clean product-containing fractions were combined and evaporated to yield 1-(6-bromo-1-hexyl)-2-piperidone as an oil (3.66 g).

Workup

  1. concentrationThe filtered, concentrated
  2. customreaction mixture
  3. customThe hexane layer was separated
  4. customevaporated to an oil
  5. customThe oil was chromatographed on silica gel
  6. additionClean product-containing fractions
  7. customevaporated

Sources & evidence

ORD record
ord-ab283c25d41244c485edc55b5d220208
Source dataset
uspto-grants-1984_02
Patent number
US04431649

Reaction notes

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