1-Bromo-3-chloropropane → 1-[(4-Chlorophenyl)methyl]-4-(3-chloropropyl)piperazine

HRID 444211Notes

Reaction equation

HRID 444211 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.Br[CH2:16][CH2:17][CH2:18][Cl:19].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([CH2:16][CH2:17][CH2:18][Cl:19])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 1348264-Chlorobenzylpiperazine

Product 1

HCID 133997271-[(4-Chlorophenyl)methyl]-4-(3-chloropropyl)piperazineYield 80%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 1-(4-chlorobenzyl)piperazine (6.32 g; 0.03 mole), 1-bromo-3-chloropropane (4.75 g; 0.03 mole), anhydrous potassium carbonate (6.25 g; 0.045 mole) and butanone (75 ml) was stirred at reflux for 3 hr, cooled and filtered. The filtrate was evaporated in vacuo, and the residue dissolved in ether and washed with water (3x). The solvent solution dried over magnesium sulphate, filtered and evaporated to yield 6.86 g (80%) of the title compound. G.L.C. (5% Dexsil 300, 100°-350° at 15°/min) showed the sample to be 99% pure. A sample was distilled b.p.0.5 150°, and the distillate had the following spectral and analytical characteristics: νmax (film) 2900, 2760, 1480, 1450, 1435 cm-1. δ (CDCl3), 1.95 (2H,m); 2.43 (10H,m); 3.42 (2H,s); 3.56 (2H,t,J 7 Hz); 7.25 (4 H,s) (Found; C, 58.32; H, 7.07; Cl, 24.37; N, 9.79; C14H20Cl2N2 requires; C, 58.34; H, 7.02; Cl, 24.69; N, 9.75%).

Workup

  1. temperatureat reflux for 3 hr
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe filtrate was evaporated in vacuo
  5. dissolutionthe residue dissolved in ether
  6. washwashed with water (3x)
  7. dry with materialThe solvent solution dried over magnesium sulphate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-e5299550edf74c19b55c159a1dee3905
Source dataset
uspto-grants-1981_04
Patent number
US04263299

Reaction notes

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