Diethyl Ether → HCID 86682761, compound

HRID 1404826Notes

Reaction equation

HRID 1404826 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[Br:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Br:14].C(OCC)C>CN(C)C=O>[Br-:8].[Br:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][N+:2]1([CH3:1])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 81001,5-DibromopentaneHCID 12291N-Methylpiperidine

Product 1

HCID 86682761HCID 86682761, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1-methylpiperidine (˜26.04 g) in dimethylformamide (˜250 mL) was added slowly to a solution of 1,5-dibromopentane (˜226.3 g) in dimethylformamide (˜50 mL) with rapid stirring. Stirring of the solution was continued overnight. The reaction mixture was then poured into diethyl ether (˜1500 mL) producing a yellow oil. The diethyl ether was decanted and the oil poured into a solution of fresh diethyl ether (˜1500 mL) with acetone (˜250 mL) and then stirred overnight. The resulting waxy solid was filtered. After drying the product (˜51.8 g, ˜60%) was confirmed to be 1-(5-bromopentyl)-1-methylpiperidin-1-ium bromide by 1H NMR.

Workup

  1. customproducing a yellow oil
  2. customThe diethyl ether was decanted
  3. additionthe oil poured into a solution of fresh diethyl ether (˜1500 mL) with acetone (˜250 mL)
  4. stirringstirred overnight
  5. filtrationThe resulting waxy solid was filtered
  6. dry with materialAfter drying the product (˜51.8 g, ˜60%)

Sources & evidence

ORD record
ord-cd27f247981c40268c7eea3ac834ec47
Source dataset
uspto-grants-2014_12
Patent number
US08916130B2

Reaction notes

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