Triethylamine → HCID 18960852, compound

HRID 257444Notes

Reaction equation

HRID 257444 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][C:12]([Cl:15])=[C:11]([CH:16]=[N:17][OH:18])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrN1C(=O)CCC1=O.[CH3:27][O:28][CH2:29][C:30]#[CH:31].C(N(CC)CC)C>CN(C)C=O.O>[C:1]([N:9]1[CH2:14][CH2:13][C:12]([Cl:15])=[C:11]([C:16]2[CH:31]=[C:30]([CH2:29][O:28][CH3:27])[O:18][N:17]=2)[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 67184N-bromobutanimideHCID 693933-MethoxypropyneHCID 86747375HCID 86747375, compound

Product 1

HCID 18960852HCID 18960852, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1-benzoyl-4-chloro-3-formyl-1,2,5,6-tetrahydropyridine oxime (5.3 g, 20 mmol) in 100 ml dry dimethylformamide was added N-bromosuccinimide (4.5 g, 25 mmol) dissolved in 20 ml dry dimethylformamide. The reaction mixture was stirred at room temperature for 1 h. Now methylpropargylether (1.5 ml, 25 mmol) and 2 ml triethylamine was added and the reaction mixture stirred at room temperature overnight. 200 ml water was added and the aqueous phase extracted with 3×50 ml ether. The combined ether extracts were washed with 2×50 ml water, dried over magnesiumsulfate and concentrated in vacuo. The compound was finally purified by column chromatography with methylenechloride/ethylacetate 4:1 as eluent. Yield: 3.5 g. M.p. 60.5°-62° C.

Workup

  1. stirringthe reaction mixture stirred at room temperature overnight
  2. extractionthe aqueous phase extracted with 3×50 ml ether
  3. washThe combined ether extracts were washed with 2×50 ml water
  4. dry with materialdried over magnesiumsulfate
  5. concentrationconcentrated in vacuo
  6. customThe compound was finally purified by column chromatography with methylenechloride/ethylacetate 4:1 as eluent

Sources & evidence

ORD record
ord-067a37debdfb4632ad4240bf961059e0
Source dataset
uspto-grants-1993_11
Patent number
US05262427

Reaction notes

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