Furfuryl Alcohol → N,N-diethyl-4-[[4-(2-furanylmethyl)-1-piperazinyl](8-quinolinyl)methyl]benzamide

HRID 1837548Notes

Reaction equation

HRID 1837548 reaction equation
[CH2:1](O)[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[CH2:20]([N:22]([CH2:48][CH3:49])[C:23](=[O:47])[C:24]1[CH:29]=[CH:28][C:27]([CH:30]([C:37]2[CH:38]=[CH:39][CH:40]=[C:41]3[C:46]=2[N:45]=[CH:44][CH:43]=[CH:42]3)[N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:26][CH:25]=1)[CH3:21].[OH-].[Na+]>C(Cl)Cl>[CH2:48]([N:22]([CH2:20][CH3:21])[C:23](=[O:47])[C:24]1[CH:29]=[CH:28][C:27]([CH:30]([N:31]2[CH2:32][CH2:33][N:34]([CH2:1][C:2]3[O:6][CH:5]=[CH:4][CH:3]=3)[CH2:35][CH2:36]2)[C:37]2[CH:38]=[CH:39][CH:40]=[C:41]3[C:46]=2[N:45]=[CH:44][CH:43]=[CH:42]3)=[CH:26][CH:25]=1)[CH3:49]

Participants

7

Reactant 5

HCID 7361Furfuryl AlcoholHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 9801260N,N-diethyl-4-(1-piperazinyl(8-quinolinyl)methyl)benzamide

Product 1

HCID 10116824N,N-diethyl-4-[[4-(2-furanylmethyl)-1-piperazinyl](8-quinolinyl)methyl]benzamideYield 54.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of furfurylalcohol (0.19 ml; 2.24 mmol) and triethylamine (0.52 ml; 3.73 mmol) in methylene chloride (4 ml) was added methanesulfonyl chloride (0.17 ml; 2.24 mmol). The mixture was stirred 1 hour at 0° C., then compound 1 (300 mg; 0.75 mmol) was added. The reaction mixture was allowed to warm to room temperature and stirred overnight, then heated to 45° C. and stirred for 1½ hours. The reaction mixture was allowed to cool to room temperature and NaOH 2N was added untill pH was basic. The mixture was extracted with methylene chloride (3×). The combined methylene chloride extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by reverse phase using 10%-25% CH3CN/H2O (TFA as the buffer) gave 197 mg of desired product (TFA salt).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. temperatureheated to 45° C.
  4. stirringstirred for 1½ hours
  5. temperatureto cool to room temperature
  6. extractionThe mixture was extracted with methylene chloride (3×)
  7. dry with materialThe combined methylene chloride extracts were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customPurification by reverse phase

Sources & evidence

ORD record
ord-53d4044516bf43b7a1f057ab31d3c764
Source dataset
uspto-grants-2004_08
Patent number
US06784181B2

Reaction notes

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