Benzaldehyde → HCID 53784190, compound

HRID 2231782Notes

Reaction equation

HRID 2231782 reaction equation
[CH3:1][NH:2][C:3](=[O:17])[CH:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5][CH2:6][CH2:7][N:8]([CH3:10])[CH3:9].[Li]CCCC.[CH:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1.CCCCCC>[CH3:1][NH:2][C:3](=[O:17])[C:4]([CH:23]([OH:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:5][CH2:6][CH2:7][N:8]([CH3:10])[CH3:9]

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 14257913HCID 14257913, compoundHCID 178418339Butyllithium

Product 1

HCID 53784190HCID 53784190, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To N-methyl-5-dimethylamino-2-phenylpentanamide (5.0 g, 0.023 mol) dissolved in 50 ml THF was added 18.1 ml of a 2.5M solution of n-BuLi in n-hexane with ice-cooling under N2. After stirring at 0° C. for 30 min, benzaldehyde (2.4 g, 0.023 mol) dissolved in 10 ml THF was added dropwise to the foregoing solution. The reaction mixture was stirred for 5 min at 0° C. and then poured into ice-cold HCl. The resulting solution was washed with Et2O, basified by adding dilute NaOH while stirring in the cold, and extracted with CHCl3. The CHCl3 extracts were combined, dried (Na2SO4), and evaporated. Chromatography of the post-evaporation residue afforded the desired compound as a mixture of diastereoisomers as an oil. Dissolution in EtOH, acidification with HCl, followed by addition of Et2O gave the hydrochloride salt as a colorless solid. [Anal. Calc'd for C21H28N2O2.HCl1/4EtOH: C, 66.17; H, 7.93; N, 7.18; Cl, 9.08. Found: C, 65.82; H, 8.02; N, 7.04; Cl 10.27.]

Workup

  1. temperaturecooling under N2
  2. additionwas added dropwise to the foregoing solution
  3. stirringThe reaction mixture was stirred for 5 min at 0° C.
  4. additionpoured into ice-cold HCl
  5. washThe resulting solution was washed with Et2O
  6. additionby adding dilute NaOH
  7. stirringwhile stirring in the cold, and
  8. extractionextracted with CHCl3
  9. dry with materialdried (Na2SO4)
  10. customevaporated

Sources & evidence

ORD record
ord-7dace54c0bfe47f28c926851c2d6a9df
Source dataset
uspto-grants-1988_11
Patent number
US04783537

Reaction notes

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