Myristyl bromide → 1-tetradecylpyrrolidine

HRID 258242Notes

Reaction equation

HRID 258242 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1>C(#N)C>[CH2:2]([N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 8208Myristyl bromideHCID 31268Pyrrolidine

Product 1

HCID 41458371-tetradecylpyrrolidineYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a 250-mL round bottom flask, equipped with a magnetic stirrer, a heating mantle and reflux condenser, were placed 1-bromotetradecane (10 g, 36 mmol), acetonitrile (100 mL) and pyrrolidine (5.1 g, 72 mmol). The reaction mixture was refluxed for 3 hrs. The reaction mixture was cooled to room temperature and was concentrated on a rotary evaporator to a residue. Water and ethyl acetate were added. The organic phase was separated and washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated to dryness affording 7.2 g (75% yield) of 1-tetradecylpyrrolidine, as a light yellow semi-solid. This intermediate was subjected to the next step without further purification.

Workup

  1. customIn a 250-mL round bottom flask, equipped with a magnetic stirrer
  2. temperaturea heating mantle and reflux condenser
  3. temperatureThe reaction mixture was refluxed for 3 hrs
  4. concentrationwas concentrated on a rotary evaporator to a residue
  5. additionWater and ethyl acetate were added
  6. customThe organic phase was separated
  7. washwashed with saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationAfter filtration
  10. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-e227f5ba402b43708822ff980e445702
Source dataset
uspto-grants-1993_11
Patent number
US05266567

Reaction notes

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