Acetic Acid → 4-[2-[1-[2-[4-(p-Toluidino)piperidin-1-yl]ethyl]cyclohexyl]ethyl]morpholine

HRID 1820298Notes

Reaction equation

HRID 1820298 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:15]([CH2:17][C:18]1([CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=O.[C:32]1([CH3:45])[CH:37]=[CH:36][C:35]([NH:38][CH:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)=[CH:34][CH:33]=1.C(O)(=O)C.C(=O)([O-])O.[Na+]>ClCCCl.C(Cl)(Cl)Cl>[C:32]1([CH3:45])[CH:33]=[CH:34][C:35]([NH:38][CH:39]2[CH2:44][CH2:43][N:42]([CH2:15][CH2:17][C:18]3([CH2:24][CH2:25][N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:41][CH2:40]2)=[CH:36][CH:37]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 23020914N-(4-Methylphenyl)-4-piperidinamineHCID 231099074-[2-[1-(Formylmethyl)cyclohexyl]ethyl]morpholine

Product 1

HCID 231099094-[2-[1-[2-[4-(p-Toluidino)piperidin-1-yl]ethyl]cyclohexyl]ethyl]morpholineYield 48%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6212ChloroformSolvent

Procedure

After adding sodium triacetoxyborohydride (579 mg, 2.73 mmol) to a solution of 4-[2-[1-(formylmethyl)cyclohexyl]ethyl]morpholine (625 mg, ca. 1.82 mmol), 4-(p-toluidino)piperidine (519 mg, 2.73 mmol) and acetic acid (0.21 mL, 3.64 mmol) in 1,2-dichloroethane (10 mL), the mixture was stirred for 3 hours. Saturated aqueous sodium hydrogencarbonate was added to the reaction mixture, and extraction was performed with chloroform. The organic layer was washed with saturated brine and dried (anhydrous sodium sulfate), and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (30 g Merck Art 9385, chloroform:methanol=1:0-10:1) to obtain the title compound as a colorless oil (346 mg) (48% yield).

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried (anhydrous sodium sulfate)
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (30 g Merck Art 9385, chloroform:methanol=1:0-10:1)

Sources & evidence

ORD record
ord-f5817cc6521a4557bc922e492ebb371d
Source dataset
uspto-grants-2009_10
Patent number
US07601843B2

Reaction notes

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