N,N,N',N'-Tetramethylethylenediamine → HCID 18616206, compound

HRID 1263450Notes

Reaction equation

HRID 1263450 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6][CH2:7][CH2:8]CCC.CN(CCN(C)C)C.[C:20]1(=O)[C:29]2[C:24](=[CH:25]C=CC=2)[CH2:23][CH2:22][CH2:21]1.C([C:33]12[C:43](CCC)=[CH:42][CH:41]=[CH:40][CH:39]1[NH:38][C:37](=O)[O:36][C:34]2=O)C>C1COCC1.[Cl-].[NH4+]>[CH2:3]([C:2]1[CH:1]=[CH:25][C:24]2[CH2:29][CH2:20][C:21]3[C:34](=[O:36])[C:33]4[CH:43]=[C:42]([CH:7]([CH3:8])[CH3:6])[CH:41]=[CH:40][C:39]=4[NH:38][C:37]=3[C:23]=2[CH:22]=1)[CH3:4]

Participants

8

Reactant 5

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8058HexaneHCID 107241-TetraloneHCID 86758894HCID 86758894, compoundHCID 178418339Butyllithium

Product 1

HCID 18616206HCID 18616206, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

To a 1.6M solution of n-butyl lithium in hexane (1.6 mL, 2.6 mmol) was added TMEDA (0.4 mL, 2.6 mmol) under argon atmosphere at room temperature with stirring. To this was added with ice cooling a solution of 1-tetralone (0.38 g, 2.6 mmol) in anhydrous THF followed by stirring for 1 hour under ice cooling. Thereafter, a solution of 1-ethyl-6-1-propylisatoic anhydride (0.3 g, 1.3 mmol) in anhydrous THF was added dropwise followed by stirring at room temperature for 1.5 hours. The reaction mixture was diluted with saturated aqueous solution of ammonium chloride. The organic layer was separated and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with saturated sodium chloride solution and dried with sodium sulfate. After removing the solvent, the residue was purified by silica gel-chromatography (chloroform) followed by crystallization from petroleum ether to give the desired compound. 1H-NMR(CDCl3)δ 1.15(3H,t,NCH2CH3), 1.33(6H,d,CH(CH3)2), 2.79-2.86(4H,m,CH2CH2), 3.07(1H,septet,CH), 4.62(2H,q,NCH2), 7.32-7.60(6H,m,Ar-H), 8.33(1H,d,H-8)

Workup

  1. stirringby stirring for 1 hour under ice cooling
  2. stirringby stirring at room temperature for 1.5 hours
  3. customThe organic layer was separated
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with saturated sodium chloride solution
  7. dry with materialdried with sodium sulfate
  8. customAfter removing the solvent
  9. customthe residue was purified by silica gel-chromatography (chloroform)
  10. customfollowed by crystallization from petroleum ether

Sources & evidence

ORD record
ord-6bff6cc2740446ebb80ca6da2248bd82
Source dataset
uspto-grants-2003_04
Patent number
US06541470B1

Reaction notes

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