Acetaldehyde → 1-Ethyl-4-(4-nitrophenyl)piperidine

HRID 2066707Notes

Reaction equation

HRID 2066707 reaction equation
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:2].[Na+].[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:20][CH:19]=1)([O-:17])=[O:16].C(=O)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([N:27]1[CH2:26][CH2:25][CH:24]([C:21]2[CH:22]=[CH:23][C:18]([N+:15]([O-:17])=[O:16])=[CH:19][CH:20]=2)[CH2:29][CH2:28]1)[CH3:2]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 159258174-(4-Nitrophenyl)piperidine

Product 1

HCID 691793941-Ethyl-4-(4-nitrophenyl)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

Sodium triacetoxyborohydride (3.1 g, 14.6 mmol, 3 equiv) is added to a cold (5° C.) solution of 4-(4-nitro-phenyl)-piperidine (1 g, 4.9 mmol) and acetaldehyde (0.82 mL, 14.6 mmol, 3 equiv) in DCM (20 mL). The reaction mixture is stirred for 1 h at 5° C. and then diluted with DCM and a saturated aqueous solution of NaHCO3. The layers are separated and the aqueous layer is extracted with DCM. The organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (DCM/MeOH+1% NH3aq, 98:2) to provide the title compound as a yellow oil. ESI-MS: 235.1 [MH]+; tR=2.64 min (purity: 85%, system 1); TLC: Rf=0.14 (DCM/MeOH+1% NH3aq, 98:2).

Workup

  1. customThe layers are separated
  2. extractionthe aqueous layer is extracted with DCM
  3. washThe organic phase is washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by silica gel column chromatography (DCM/MeOH+1% NH3aq, 98:2)

Sources & evidence

ORD record
ord-717b571d9951450c8ded46d555cd1de1
Source dataset
uspto-grants-2012_10
Patent number
US08293746B2

Reaction notes

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