Triethylamine → HCID 60704011, compound

HRID 1642108Notes

Reaction equation

HRID 1642108 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[CH3:11][O:12][C:13](=[O:20])[CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:17]2[CH2:18][CH2:19][CH:14]([C:13]([O:12][CH3:11])=[O:20])[CH2:15][CH2:16]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 699934-Methyloxybenzyl chlorideHCID 424914Methyl isonipecotateHCID 516892Sodium Bicarbonate

Product 1

HCID 60704011HCID 60704011, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Methoxybenzyl chloride (1.10 g, 6.98 mmol) was added dropwise to a solution of isonipecotic acid methyl ester (1.00 g, 6.98 mmol) and triethylamine (1.40 g, 14 mmol) in THF (30 ml), and stirring was carried out for 72 h at 60° C. 5% sodium hydrogen carbonate solution (50 ml) was then added to the reaction mixture, and extraction with ethyl acetate (3×50 ml) was carried out. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography with cyclohexane/ethyl acetate (2:1).

Workup

  1. dry with materialThe combined organic phases were dried over sodium sulfate
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography with cyclohexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-29fa6f8da3034c4e97db72c3f70a821a
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

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