Diisopropylamine → HCID 59424371, compound

HRID 1172355Notes

Reaction equation

HRID 1172355 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.CCCCC.[CH2:18]([N:25]1[CH2:30][CH2:29][CH:28]([CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[N+:36]([C:39]1[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=1[CH:41]=[O:42])([O-:38])=[O:37]>O1CCCC1>[CH2:18]([N:25]1[CH2:30][CH2:29][CH:28]([CH:31]([CH:41]([OH:42])[C:40]2[CH:43]=[CH:44][CH:45]=[CH:46][C:39]=2[N+:36]([O-:38])=[O:37])[C:32]([O:34][CH3:35])=[O:33])[CH2:27][CH2:26]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 5

HCID 7912DiisopropylamineHCID 8003PentaneHCID 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 (24.87 mmoles; 3.50 mL) was dissolved in tetrahydrofuran (30.00 mL). Mixture was cooled to −78° C. 2.5 M butyllithium in pentane (24.50 mmoles; 9.80 mL) was added to the mixture drop-wise. Reaction was stirred at −78° C. for 15 minutes. A solution of methyl 2-(1-benzylpiperidin-4-yl)acetate (22.24 mmoles; 5.50 g) in 8 mL THF was then added to the mixture dropwise over 20 minutes. Reaction stirred at −78° C. for 45 minutes. A solution of 2-nitrobenzaldehyde (24.48 mmoles; 3.70 g) in 5 mL THF was then added to the mixture dropwise over 15 minutes. Reaction was stirred at −78° C. for 30 minutes. Reaction was quenched with saturated aqueous ammonium chloride. Mixture was warmed to room temperature. Extracted from the mixture 2× EtOAc. Combined organics were dried (magnesium sulfate), filtered, then concentrated. Silica gel chromatography afforded the desired product in 89% yield as light yellow foam. MS m/e (M+H)+=399.3.

Workup

  1. customReaction
  2. customReaction
  3. stirringstirred at −78° C. for 45 minutes
  4. customReaction
  5. stirringwas stirred at −78° C. for 30 minutes
  6. customReaction
  7. customwas quenched with saturated aqueous ammonium chloride
  8. temperatureMixture was warmed to room temperature
  9. extractionExtracted from the mixture 2× EtOAc
  10. dry with materialCombined organics were dried (magnesium sulfate)
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-4f93b3ec4cec4533bb4790f7ae2425d9
Source dataset
uspto-grants-2010_11
Patent number
US07834007B2

Reaction notes

Loading…