Triethylamine → HCID 60704011, compound

HRID 424616Notes

Reaction equation

HRID 424616 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>[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

6

Reactant 4

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

Product 1

HCID 60704011HCID 60704011, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

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 the mixture was stirred at 60° C. for 72 h. 5% strength sodium bicarbonate solution (50 ml) was then added to the reaction mixture and the mixture was extracted with ethyl acetate (3×50 ml). The combined organic phases were dried with sodium sulfate and concentrated i. vac. The residue was purified by flash chromatography with cyclohexane/ethyl acetate (2:1).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×50 ml)
  2. dry with materialThe combined organic phases were dried with sodium sulfate
  3. concentrationconcentrated i
  4. customThe residue was purified by flash chromatography with cyclohexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-8ab3399ef0104d96bed5280e18f6d641
Source dataset
uspto-grants-2012_01
Patent number
US08106055B2

Reaction notes

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