Diisopropylamine → HCID 59424371, compound

HRID 501976Notes

Reaction equation

HRID 501976 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([N:20]1[CH2:25][CH2:24][CH:23]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[N+:31]([C:34]1[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=1[CH:36]=[O:37])([O-:33])=[O:32]>O1CCCC1>[CH2:13]([N:20]1[CH2:25][CH2:24][CH:23]([CH:26]([CH:36]([OH:37])[C:35]2[CH:38]=[CH:39][CH:40]=[CH:41][C:34]=2[N+:31]([O-:33])=[O:32])[C:27]([O:29][CH3:30])=[O:28])[CH2:22][CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 111012-NitrobenzaldehydeHCID 11011492Methyl 1-(phenylmethyl)-4-piperidineacetateHCID 178418339Butyllithium

Product 1

HCID 59424371HCID 59424371, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

Diisopropylamine (3.50 mL, 24.9 mmol) was dissolved in tetrahydrofuran (30 mL). The mixture was cooled to −78° C. Butyllithium (2.5 M in pentane, 9.8 mL, 24.5 mmol) was added to the mixture dropwise, and the reaction stirred at −78° C. for 15 min. A solution of methyl 2-(1-benzylpiperidin-4-yl)acetate (5.50 g, 22.2 mmol) in THF (8 mL) was then added to the mixture dropwise over 20 minutes. The reaction was stirred at −78° C. for 45 minutes. A solution of 2-nitrobenzaldehyde (3.70 g, 24.5 mmol) in THF (5 mL) was then added to the mixture dropwise over 15 minutes. The reaction was stirred at −78° C. for 30 minutes and quenched by the addition of saturated aqueous ammonium chloride. The resulting mixture was warmed to room temperature, extracted with ethyl acetate (2×). The combined organics were dried (magnesium sulfate), filtered, and concentrated. Silica gel chromatography afforded the desired product in 89% yield as light yellow foam. Mass spec.: 399.3 (MH)+.

Workup

  1. stirringThe reaction was stirred at −78° C. for 45 minutes
  2. stirringThe reaction was stirred at −78° C. for 30 minutes
  3. customquenched by the addition of saturated aqueous ammonium chloride
  4. temperatureThe resulting mixture was warmed to room temperature
  5. extractionextracted with ethyl acetate (2×)
  6. dry with materialThe combined organics were dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6be9bcce892b4351abe6712a8b34acd5
Source dataset
uspto-grants-2010_08
Patent number
US07772244B2

Reaction notes

Loading…