N-Benzylnormechlorethamine → 8-(4-Benzyl-piperazin-1-yl)quinoline

HRID 992037Notes

Reaction equation

HRID 992037 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.Cl[CH2:13][CH2:14][N:15]([CH2:23][CH2:24]Cl)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[Na+]>C(O)CCC>[CH2:16]([N:15]1[CH2:23][CH2:24][N:1]([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][CH:8]=[CH:7]3)[CH2:13][CH2:14]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 5928N-BenzylnormechlorethamineHCID 113598-AminoquinolineHCID 14798Sodium Hydroxide

Product 1

HCID 184140838-(4-Benzyl-piperazin-1-yl)quinolineYield 45.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 8-amino-quinoline (12.91 g, 89 mmol) and bis(2-chloroethyl)benzylamine (25.95 g, 112 mmol) in n-butanol (65 ml) was allowed to heat at 85° C. for 11 hours. The mixture was poured into 50% sodium hydroxide, extracted with methylene chloride and water. The organic layer was dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under vacuum. Chromatography (methanol-methylene chloride) afforded 12.34 g of product as a solid: mp 116.5-118° C.

Workup

  1. extractionextracted with methylene chloride and water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-6ed4bc756fc9438fb8dc6cd063a66698
Source dataset
uspto-grants-2002_10
Patent number
US06465482B2

Reaction notes

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