Triethylamine → N-(4-Chloro-phenyl)-4-{3-[4-(3,3-dimethyl-butyl)-piperazin-1-yl]-propoxy}-3-fluoro-N-methyl-benzamide

HRID 220909Notes

Reaction equation

HRID 220909 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH3:30])[C:11](=[O:29])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[C:14]([F:28])[CH:13]=2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH3:38][C:39]([CH3:44])([CH3:43])[CH2:40][CH:41]=O.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH3:30])[C:11](=[O:29])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][N:22]3[CH2:23][CH2:24][N:25]([CH2:41][CH2:40][C:39]([CH3:44])([CH3:43])[CH3:38])[CH2:26][CH2:27]3)=[C:14]([F:28])[CH:13]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 763353,3-DimethylbutanalHCID 5003444Sodium cyanoborohydrideHCID 67287537N-(4-Chloro-phenyl)-3-fluoro-N-methyl-4-(3-piperazin-1-yl-propoxy)-benzamide Dihydrochloride

Product 1

HCID 57555354N-(4-Chloro-phenyl)-4-{3-[4-(3,3-dimethyl-butyl)-piperazin-1-yl]-propoxy}-3-fluoro-N-methyl-benzamideYield 37%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

N-(4-Chloro-phenyl)-3-fluoro-N-methyl-4-(3-piperazin-1-yl-propoxy)-benzamide dihydrochloride from Example E71.2 (184 mg, 0.4 mmol) was dissolved in methanol (4.95 ml) and triethylamine (0.167 ml, 1.2 mmol). Acetic acid (0.05 ml) then 3,3-dimethylbutyraldehyde (46 mg, 0.44 mmol) were added and the mixture was stirred for 1 h at room temperature. Sodium cyanoborohydride (31 mg, 0.5 mmol) was added and the mixture was stirred for 20 h at room temperature then concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 10% methanol:90% dichloromethane) to give a white foam identified as the title compound (77 mg, 37%).

Workup

  1. stirringthe mixture was stirred for 20 h at room temperature
  2. concentrationthen concentrated in vacuo
  3. customThe residue was purified by flash chromatography on silica gel (eluant; 10% methanol:90% dichloromethane)
  4. customto give a white foam

Sources & evidence

ORD record
ord-6661d6a6578a473e8610df02fdbf7da4
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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