3,3-Dimethylbutanal → 4-{2-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-ethoxy}-3-methyl-benzoic Acid Methyl Ester

HRID 220844Notes

Reaction equation

HRID 220844 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH:4]=O.Cl.Cl.[CH3:10][O:11][C:12](=[O:29])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[C:15]([CH3:28])[CH:14]=1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[CH3:10][O:11][C:12](=[O:29])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][N:25]([CH2:4][CH2:3][C:2]([CH3:7])([CH3:6])[CH3:1])[CH2:24][CH2:23]2)=[C:15]([CH3:28])[CH:14]=1

Participants

5

Reactant 3

HCID 763353,3-DimethylbutanalHCID 5003444Sodium cyanoborohydrideHCID 67053806HCID 67053806, compound

Product 1

HCID 575552114-{2-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-ethoxy}-3-methyl-benzoic Acid Methyl EsterYield 34%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

3,3-Dimethylbutyraldehyde (54 mg, 0.53 mmol) was added to a solution of 3-methyl-4-(2-piperazin-1-yl-ethoxy)-benzoic acid methyl ester dihydrochloride from Example E40.2 (146 mg, 0.42 mmol) in methanol/acetic acid (99:1, v/v, 10 ml) and the mixture was stirred at room temperature for 1 h. Sodium cyanoborohydride (42 mg, 0.69 mmol) was added, and the mixture was stirred at room temperature for 18 h then concentrated in vacuo. The residue was dissolved in EtOAc, washed with saturated NaHCO3, water then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel through an isolute (eluant; EtOAc) to yield the title compound (64 mg, 34%).

Workup

  1. stirringthe mixture was stirred at room temperature for 18 h
  2. concentrationthen concentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with saturated NaHCO3, water
  5. dry with materialbrine, dried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel through an isolute (eluant; EtOAc)

Sources & evidence

ORD record
ord-ec7264c6e02a429682a23e3cc7306a2b
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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