Sulfuric Acid → HCID 49779837, compound

HRID 1773255Notes

Reaction equation

HRID 1773255 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:10][CH2:11][C:12]2[CH:13]=[N:14][C:15]([CH3:18])=[CH:16][CH:17]=2)N)=[CH:4][CH:3]=1.[CH3:19][N:20]1[CH2:25][CH2:24][C:23](=O)[CH2:22][CH:21]1[CH3:27].S(=O)(=O)(O)O.C([O-])(O)=O.[Na+]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]([CH2:10][CH2:11][C:12]3[CH:13]=[N:14][C:15]([CH3:18])=[CH:16][CH:17]=3)[C:23]3[CH2:22][CH:21]([CH3:27])[N:20]([CH3:19])[CH2:25][C:24]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 124240391,2-Dimethylpiperidin-4-oneHCID 66601555HCID 66601555, compound

Product 1

HCID 49779837HCID 49779837, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 1-(4-chlorophenyl)-1-(2-(6-methylpyridin-3-yl)ethyl)hydrazine (1 g, 3.83 mmol) in dioxane (10 mL) was added 1,2-dimethylpiperidin-4-one (0.538 g, 4.59 mmol) and 0.5 mL of conc. sulfuric acid at RT. The reaction was heated at 90° C. for 2 h. After completion of reaction, the mixture was basified by addition of a saturated solution of NaHCO3. The product was extracted with EtOAc, and the organic layer washed with water, dried over sodium sulfate and concentrated. The solid obtained was purified by HPLC. 1HNMR (CD3OD, TFA salt) d (ppm): 8.30 (s, 1H), 8.05 (d, 1H), 7.64 (d, 1H), 7.50 (s, 1H), 7.24 (d, 1H), 7.10 (d, 1H), 4.50 (t, 2H), 4.40 (m, 1H), 4.0 (m, 1H), 3.80 (m, 1H), 3.30 (m, 3H), 3.0 (m, 4H), 2.62 (s, 3H), 1.50 (d, 3H).

Workup

  1. customAfter completion of reaction
  2. extractionThe product was extracted with EtOAc
  3. washthe organic layer washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe solid obtained
  7. customwas purified by HPLC

Sources & evidence

ORD record
ord-e7d56978e9ec4cfd87b7977ddfe98cab
Source dataset
uspto-grants-2016_02
Patent number
US09255094B2

Reaction notes

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