4,7-Dichloroquinoline → HCID 11670888, compound

HRID 2167058Notes

Reaction equation

HRID 2167058 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][NH2:26])[CH2:19][CH2:18]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:26][CH2:25][CH2:24][CH2:23][N:20]3[CH2:19][CH2:18][N:17]([CH2:16][CH2:15][CH2:14][NH:13][C:2]4[C:11]5[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=5)[N:5]=[CH:4][CH:3]=4)[CH2:22][CH2:21]3)=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 68664,7-DichloroquinolineHCID 11430Potassium CarbonateHCID 816291,4-Bis(3-aminopropyl)piperazine

Product 1

HCID 11670888HCID 11670888, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4,7-dichloroquinoline (1.58 g, 8.0 mmol) and 1,4-bis(3-aminopropyl)piperazine (0.33 mL, 1.6 mmol) in DMF (5 mL) is refluxed (160° C.) for 18 h in the presence of K2CO3 (1.77 g, 12.8 mmol). After evaporation, the media is diluted with HCl 1M, and washed with ethyl acetate. Aqueous layer is alcalinised with NaHCO3, extracted with CH2Cl2, and dried over MgSO4. Crude compound is purified by precipitation in ethyl acetate.

Workup

  1. customAfter evaporation
  2. additionthe media is diluted with HCl 1M
  3. washwashed with ethyl acetate
  4. extractionextracted with CH2Cl2
  5. dry with materialdried over MgSO4
  6. customCrude compound is purified by precipitation in ethyl acetate

Sources & evidence

ORD record
ord-27e29f203d3d4ae099ebd97919962b4e
Source dataset
uspto-grants-2015_06
Patent number
US09044478B2

Reaction notes

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