1-Benzylpiperidin-4-ol → HCID 11653839, compound

HRID 1171807Notes

Reaction equation

HRID 1171807 reaction equation
[CH2:1]([NH:6][C:7]([C:9]1[N:10]=[N:11][C:12](Cl)=[CH:13][CH:14]=1)=[O:8])[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:16]([N:23]1[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CC([O-])(C)C.[K+]>O1CCOCC1>[CH2:1]([NH:6][C:7]([C:9]1[N:10]=[N:11][C:12]([O:29][CH:26]2[CH2:27][CH2:28][N:23]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:24][CH2:25]2)=[CH:13][CH:14]=1)=[O:8])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 784611-Benzylpiperidin-4-olHCID 23665647Potassium tert-butoxide2×HCID 442031536-Chloropyridazine-3-carboxylic acid pentylamide

Product 1

HCID 11653839HCID 11653839, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 6-chloropyridazine-3-carboxylic acid pentylamide (0.530 g, 2.33 mmol) and 1-benzylpiperidin-4-ol (0.399 g, 2.33 mmol) in dioxane (20 mL) was added KOtBu (0.288 g, 2.56 mmol). The colourless reaction mixture turned to bright red upon the addition of KOtBu. The reaction mixture was stirred at room temperature for 16 hours, then concentrated in vacuo. The residue was diluted with ethyl acetate, washed with water, dried over Na2SO4, filtered and concentrated. The crude material was purified by column chromatography to afford the title compound in 28% yield (0.100 g). The solid material was triturated with ether give 22.7 mg of product as a colourless solid. M.p. 127-130° C. 1H NMR (300 MHz, CDCl3) δ 8.15 (d, J=9.3 Hz, 1H), 7.91 (t, J=5.1 Hz, 1H), 7.31 (m, 5H), 7.02 (d, J=9.3 Hz, 1H), 5.34 (septet, J=4.5 Hz, 1H), 3.51 (s, 2H), 3.44 (q, J=6.9 Hz, 2H), 2.79-2.73 (m, 2H), 2.35-2.27 (m, 2H), 2.15-2.09 (m, 2H), 1.93-1.83 (m, 2H), 1.62-1.54 (m, 2H), 1.36-1.29 (m, 4H), 0.89-0.85 (m, 3H). 13C NMR (75 MHz, CDCl3) δ 165.9, 162.5, 148.6, 138.4, 129.6, 129.1, 128.7, 128.3, 127.1, 118.6, 73.8, 62.9, 50.8, 39.5, 30.8, 29.2, 29.1, 22.4, 14.0. MS (ES+) m/z 363 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-370532435ced4560beb53168020d751d
Source dataset
uspto-grants-2010_11
Patent number
US07829712B2

Reaction notes

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