Propanal → 1-[3-(4-Propylpiperazin-1-yl)-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]ethanone

HRID 32209Notes

Reaction equation

HRID 32209 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]([C:23](=[O:25])[CH3:24])[CH:10]=[CH:11][C:12]=2[CH:13]2[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]([CH3:22])([CH3:21])[CH2:14]2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH:26](=O)[CH2:27][CH3:28].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(OCC)C.O1CCCC1>[CH2:26]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:8]=[C:9]([C:23](=[O:25])[CH3:24])[CH:10]=[CH:11][C:12]=2[CH:13]2[CH2:14][C:15]([CH3:22])([CH3:21])[CH2:16][C:17]([CH3:19])([CH3:20])[CH2:18]2)[CH2:2][CH2:3]1)[CH2:27][CH3:28]

Participants

7

Reactant 4

HCID 527PropanalHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 231416551-[3-Piperazin-1-yl-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]ethanone

Product 1

HCID 231418081-[3-(4-Propylpiperazin-1-yl)-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]ethanone

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-[3-piperazin-1-yl-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]ethanone (19 mg, 0.0555 mmol) produced in Example (82b), propionaldehyde (0.0119 mL, 0.166 mmol) and tetrahydrofuran (0.3 mL) was added sodium triacetoxyborohydride (35 mg, 0.166 mmol), followed by stirring for 1 hour at room temperature. Saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture and extraction was performed with diethyl ether. The solvent was distilled off by nitrogen stream to the separated organic layer. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 1-[3-(4-propylpiperazin-1-yl)-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]ethanone.

Workup

  1. distillationThe solvent was distilled off by nitrogen stream to the separated organic layer
  2. customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-441437e0b43042d4840c8e909f830515
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Reaction notes

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