1-Bromo-3-chloropropane → HCID 69482970, compound

HRID 397232Notes

Reaction equation

HRID 397232 reaction equation
[CH2:1]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[Br:17][CH2:18][CH2:19][CH2:20][Cl:21]>CO>[Br-:17].[Cl:21][CH2:20][CH2:19][CH2:18][N+:11]1([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 80061-Bromo-3-chloropropaneHCID 4649960HCID 4649960, compound

Product 1

HCID 69482970HCID 69482970, compoundYield 800.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

N-decylpiperidine was synthesized by reacting 45.7 g piperidine with 118.7 g 1-bromodecane in 237 mL acetone in the presence of 74 g potassium carbonate. After refluxing this reaction mixture at 55° C. for 24 hr, it was filtered and acetone was removed from the filtrate to yield 61 g N-decylpiperidine. 5 g N-decylpiperidine and 42 g 1-bromo-3-chloropropane were dissolved in 50 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 tert butylmethyl ether with stirring and then the mixture was allowed to stand for 6 hr. The white precipitate thus formed was filtered and was dried at 40° C. under vacuum for 24 hr yielding 68 g (3-chloropropyl)decylpiperidinium bromide as a light yellow solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. custommethanol was removed under reduced pressure
  3. additionThe residue was poured into 2 L tert butylmethyl ether
  4. customThe white precipitate thus formed
  5. filtrationwas filtered
  6. customwas dried at 40° C. under vacuum for 24 hr

Sources & evidence

ORD record
ord-dee3396cea4e4f5093c97670e2ec6098
Source dataset
uspto-grants-2003_08
Patent number
US06610283B1

Reaction notes

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