Triethylamine → HCID 18960861, compound

HRID 257445Notes

Reaction equation

HRID 257445 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)[CH2:23][CH2:22][C:21]1=O.BrC(C)=C.C(N(CC)CC)C>CN(C)C=O>[C:1]([N:9]1[CH2:14][CH2:13][C:12]([Cl:15])=[C:11]([C:16]2[CH:21]=[C:22]([CH3:23])[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

6

Reactant 4

HCID 8471TriethylamineHCID 112022-BromopropeneHCID 67184N-bromobutanimideHCID 86747375HCID 86747375, compound

Product 1

HCID 18960861HCID 18960861, compound

Reagents, catalysts & solvents 1

HCID 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 2-bromopropene (2.2 ml, 25 mmol) and 4 ml triethylamine were added and the reaction mixture stirred at room temperature for 48 h. The compound was purified as described for 1-Benzoyl-4-chloro-3-(5-methoxymethyl-3-isoxazolyl)-1,2,5,6-tetrahydropyridine. Yield: 3.1 g. M.p. 86°-87° C.

Workup

  1. stirringthe reaction mixture stirred at room temperature for 48 h
  2. customThe compound was purified

Sources & evidence

ORD record
ord-ebfae2c616264d9cb038fa4c549ad1b4
Source dataset
uspto-grants-1993_11
Patent number
US05262427

Reaction notes

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