1-Bromo-3-chloropropane → 1-(4-Chlorobenzyl)-4-(3-chloropropyl)homopiperazine

HRID 2290899

Reaction equation

HRID 2290899 reaction equation
Br[CH2:2][CH2:3][CH2:4][Cl:5].[Cl:6][C:7]1[CH:20]=[CH:19][C:10]([CH2:11][N:12]2[CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:9][CH:8]=1.[OH-].[K+]>CS(C)=O>[Cl:6][C:7]1[CH:20]=[CH:19][C:10]([CH2:11][N:12]2[CH2:18][CH2:17][CH2:16][N:15]([CH2:2][CH2:3][CH2:4][Cl:5])[CH2:14][CH2:13]2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14797Potassium HydroxideHCID 156343771-[(4-Chlorophenyl)methyl]-1,4-diazepane

Product 1

HCID 201531881-(4-Chlorobenzyl)-4-(3-chloropropyl)homopiperazineYield 42%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

15.7 g of 1-bromo-3-chloropropane were added to a cooled solution of 15.0 g of 1-(4-chlorobenzyl)homopiperazine and 12.0 g of potassium hydroxide in 50 ml of dimethyl sulfoxide. The mixture was stirred at 5°-10° C. for one hour, and then an additional 30 minutes at room temperature. After the addition of ice water, the product was extracted with ether, and the extract was dried (magnesium sulfate) and concentrated in vacuo. Final purification was effected on a silica gel column (methylene chloride:methanol, 9:1), and the solvent was removed in vacuo to give 8.4 g (42% of theory) of 1-(4-chlorobenzyl)-4-(3-chloropropyl)homopiperazine as an oil.

Workup

  1. customan additional 30 minutes
  2. customat room temperature
  3. extractionthe product was extracted with ether
  4. dry with materialthe extract was dried (magnesium sulfate)
  5. concentrationconcentrated in vacuo
  6. customFinal purification
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5ccc732570e64ea09e94a3855cb22b8d
Source dataset
uspto-grants-1986_10
Patent number
US04618677

Linked notes

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