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

HRID 1245246Notes

Reaction equation

HRID 1245246 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

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

Sources & evidence

ORD record
ord-cf910324afc34a96b664fbf3bdcb21b7
Source dataset
uspto-grants-2006_10
Patent number
US07125547B2

Reaction notes

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