Triethylamine → (E)-1-[4-(3-Methoxy-2-methyl-4-pyridyl)piperazin-1-yl]-4-methyl-pent-2-en-1-one

HRID 333963

Reaction equation

HRID 333963 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:15])=[N:5][CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(N(CC)CC)C.[CH3:23][CH:24]([CH3:30])/[CH:25]=[CH:26]/[C:27](Cl)=[O:28]>ClCCl>[CH3:1][O:2][C:3]1[C:4]([CH3:15])=[N:5][CH:6]=[CH:7][C:8]=1[N:9]1[CH2:10][CH2:11][N:12]([C:27](=[O:28])/[CH:26]=[CH:25]/[CH:24]([CH3:30])[CH3:23])[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10986269(E)-4-methylpent-2-enoyl ChlorideHCID 668356131-(3-Methoxy-2-methyl-4-pyridyl)piperazine

Product 1

HCID 56949086(E)-1-[4-(3-Methoxy-2-methyl-4-pyridyl)piperazin-1-yl]-4-methyl-pent-2-en-1-oneYield 7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(3-Methoxy-2-methyl-4-pyridyl)piperazine (20.7 mg, 0.1 mmol) was dissolved in dichloromethane (1 ml), triethylamine was added (1 ml of a 0.12 M solution in dichloromethane) followed by a solution of (E)-4-methylpent-2-enoyl chloride (1 ml, 0.12 M in dichloromethane). The mixture was shaken briefly, washed with 5% sodium bicarbonate solution (2×), water and evaporated to dryness. The raw product was purified by preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile) to yield 2.2 mg of a solid (0.007 mmol, 7%).

Workup

  1. washwashed with 5% sodium bicarbonate solution (2×), water
  2. customevaporated to dryness
  3. customThe raw product was purified by preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile)

Sources & evidence

ORD record
ord-ca634ec73b514dff8534f717029a5b91
Source dataset
uspto-grants-2014_11
Patent number
US08883791B2

Linked notes

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