Dichloromethane → N,N-diethyl-4-[[4-(2-thiophenylmethyl)-1-piperazinyl](8-quinolinyl)methyl]benzamide Dihydrochloride

HRID 1837549Notes

Reaction equation

HRID 1837549 reaction equation
[CH2:1]([N:3]([CH2:29][CH3:30])[C:4](=[O:28])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:18]2[CH:19]=[CH:20][CH:21]=[C:22]3[C:27]=2[N:26]=[CH:25][CH:24]=[CH:23]3)[N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:7][CH:6]=1)[CH3:2].[S:31]1[CH:35]=[CH:34][CH:33]=[C:32]1[CH:36]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].C(Cl)[Cl:55]>C(O)(=O)C>[ClH:55].[ClH:55].[CH2:29]([N:3]([CH2:1][CH3:2])[C:4](=[O:28])[C:5]1[CH:6]=[CH:7][C:8]([CH:11]([N:12]2[CH2:13][CH2:14][N:15]([CH2:36][C:32]3[S:31][CH:35]=[CH:34][CH:33]=3)[CH2:16][CH2:17]2)[C:18]2[CH:19]=[CH:20][CH:21]=[C:22]3[C:27]=2[N:26]=[CH:25][CH:24]=[CH:23]3)=[CH:9][CH:10]=1)[CH3:30]

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 73642-ThiophenecarboxaldehydeHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 9801260N,N-diethyl-4-(1-piperazinyl(8-quinolinyl)methyl)benzamide

Product 1

HCID 22677866N,N-diethyl-4-[[4-(2-thiophenylmethyl)-1-piperazinyl](8-quinolinyl)methyl]benzamide Dihydrochloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of compound 1 (0.99 mmol) in methylene chloride (10 ml) was added 2-thiophenecarboxaldehyde (190 ul; 1.98 mmol) followed by acetic acid (0.1 ml; 1%). The mixture was stirred 30 minutes then sodium triacetoxyborohydride (0.63 g; 2.97 mmol) was added and the reaction mixture stirred overnight. The reaction mixture was neutralized with sodium hydroxide 2N and 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%-30% CH3CN/H2O (TFA as the buffer) gave 115 mg of desired product (TFA salt).

Workup

  1. stirringthe reaction mixture stirred overnight
  2. extractionextracted with methylene chloride (3×)
  3. dry with materialThe combined methylene chloride extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by reverse phase

Sources & evidence

ORD record
ord-5aac26280a224f60957edab11a17f1e9
Source dataset
uspto-grants-2004_08
Patent number
US06784181B2

Reaction notes

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