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

HRID 1820290Notes

Reaction equation

HRID 1820290 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:15]1([CH3:28])[CH:20]=[CH:19][C:18]([NH:21][CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:17][CH:16]=1.[CH:29]([CH2:31][C:32]1([CH2:38][CH2:39][N:40]2[C:44](=[O:45])[C:43]3=[CH:46][CH:47]=[CH:48][CH:49]=[C:42]3[C:41]2=[O:50])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)=O.C(O)(=O)C.C(=O)([O-])O.[Na+]>ClCCCl>[C:15]1([CH3:28])[CH:16]=[CH:17][C:18]([NH:21][CH:22]2[CH2:27][CH2:26][N:25]([CH2:29][CH2:31][C:32]3([CH2:38][CH2:39][N:40]4[C:44](=[O:45])[C:43]5=[CH:46][CH:47]=[CH:48][CH:49]=[C:42]5[C:41]4=[O:50])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]3)[CH2:24][CH2:23]2)=[CH:19][CH:20]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 23020914N-(4-Methylphenyl)-4-piperidinamineHCID 23109901N-[2-[1-(formylmethyl)cyclohexyl]ethyl]phthalimide

Product 1

HCID 23109896N-[2-[1-[2-[4-(p-Toluidino)piperidin-1-yl]ethyl]cyclohexyl]ethyl]phthalimideYield 108.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

After adding sodium triacetoxyborohydride (0.82 g, 3.85 mmol) to a solution of 4-(p-toluidino)piperidine (0.73 g, 3.85 mmol), N-[2-[1-(formylmethyl)cyclohexyl]ethyl]phthalimide (0.77 g, 2.57 mmol) and acetic acid (0.30 mL, 5.14 mmol) in 1,2-dichloroethane (10 mL), the mixture was stirred at room temperature for 1.5 hours. Saturated aqueous sodium hydrogencarbonate was then added, and extraction was performed with chloroform-ethanol (10:1). After drying (anhydrous sodium sulfate), the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (25 g Merck Art 9385, chloroform:methanol=20:1) to obtain the title compound as a colorless oil (1.32 g).

Workup

  1. extractionextraction
  2. dry with materialAfter drying (anhydrous sodium sulfate)
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (25 g Merck Art 9385, chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-72a61791c9db43b5bf9b16751be1ca19
Source dataset
uspto-grants-2009_10
Patent number
US07601843B2

Reaction notes

Loading…