1-Bromo-3-chloropropane → HCID 69484213, compound

HRID 2086516Notes

Reaction equation

HRID 2086516 reaction equation
[CH2:1]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Br:18][CH2:19][CH2:20][CH2:21][Cl:22]>CO>[Br-:18].[Cl:22][CH2:21][CH2:20][CH2:19][N+:13]1([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 80061-Bromo-3-chloropropaneHCID 37320212915-94-8

Product 1

HCID 69484213HCID 69484213, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Pyrrolidine (47 g), 1-bromododecane (149.5 g) and potassium carbonate (83 g) were added to 560 mL of acetone. The reaction mixture was heated to 55° C. for 24 hr. then filtered. Solvent was removed from the filtrate, yielding 92 g of N-dodecylpyrrolidine. N-dodecylpyrrolidine (80 g) and 1-bromo-3-chloropropane (52.6 g) were dissolved in 133 mL of methanol and the reaction mixture was heated to 65° C. for 18 hr. After cooling to room temperature, methanol was removed under reduced pressure. The residue was poured into 2 L of diethylether with stirring and the mixture was allowed to stand for another 6 hr. The white precipitate was filtered and dried at 40° C. under a vacuum for 24 hr yielding 85 g of (3-chloropropyl)dodecylpyrrolidinium bromide as a white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. custommethanol was removed under reduced pressure
  3. additionThe residue was poured into 2 L of diethylether
  4. filtrationThe white precipitate was filtered
  5. customdried at 40° C. under a vacuum for 24 hr

Sources & evidence

ORD record
ord-44077a2dc3964fd7a55c95bb269b8f6d
Source dataset
uspto-grants-2004_04
Patent number
US06726905B1

Reaction notes

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