Sodium Hydroxide → N,N-diethyl-4-[[4-(3-thienylmethyl)-1-piperazinyl](8-quinolinyl)methyl]benzamide

HRID 1837547Notes

Reaction equation

HRID 1837547 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][C:33]([CH:36]=O)=[CH:32]1.C([BH3-])#N.[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[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:33]3[CH:34]=[CH:35][S:31][CH:32]=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 4

HCID 14798Sodium HydroxideHCID 681353-ThiophenecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 9801260N,N-diethyl-4-(1-piperazinyl(8-quinolinyl)methyl)benzamide

Product 1

HCID 9870536N,N-diethyl-4-[[4-(3-thienylmethyl)-1-piperazinyl](8-quinolinyl)methyl]benzamideYield 52.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of compound 1 (500 mg; 0.99 mmol) in methanol (10 ml) was added thiophene 3-carboxaldehyde (104 ul; 1.19 mmol) followed by acetic acid (0.1 ml; 1%) and sodium cyano borohydride (186.6 mg; 2.97 mmol). The reaction mixture was stirred overnight, then sodium hydroxide 2N was added and the mixture 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 258 mg of desired product (TFA salt).

Workup

  1. extractionthe mixture extracted with methylene chloride (3×)
  2. dry with materialThe combined methylene chloride extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by reverse phase

Sources & evidence

ORD record
ord-98e17ba9ea61465f989c7e8985e4b939
Source dataset
uspto-grants-2004_08
Patent number
US06784181B2

Reaction notes

Loading…