1-Butanol → HCID 53215238, compound

HRID 1027144Notes

Reaction equation

HRID 1027144 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[CH3:9][C:10]1([CH3:19])[CH2:15][CH:14]([NH2:16])[CH2:13][C:12]([CH3:18])([CH3:17])[NH:11]1.C(O)CCC>O.C(Cl)Cl>[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH:16][CH:14]2[CH2:15][C:10]([CH3:19])([CH3:9])[NH:11][C:12]([CH3:18])([CH3:17])[CH2:13]2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 2631-ButanolHCID 375244-Amino-2,2,6,6-tetramethylpiperidineHCID 673313,6-Dichloropyridazine

Product 1

HCID 53215238HCID 53215238, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3,6-dichloropyridazine (6.26 g, 42 mmol) and 2,2,6,6-tetramethylpiperidin-4-amine (14.7 mL, 84 mmol) was stirred at 120° C. for 1 h, neat. To this crude mixture was added n-butanol (40 mL), and the reaction was stirred at 120° C. for 1 h. The crude reaction mixture was cooled to room temperature and diluted in water and CH2Cl2. The organic layer was dried over MgSO4, filtered, and concentrated. The crude material was recrystallized from CH3CN to give 6-chloro-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine, Intermediate 1-2 (7.3 g) as an off-white solid. LCMS Rt=1.10 min (condition B), MS (M+1)=269.2. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.08 (d, J=9.3 Hz, 1H), 6.54 (d, J=9.3 Hz, 1H), 4.53 (d, J=7.6 Hz, 1H), 4.05-4.26 (m, 1H), 1.98 (dd, J=12.6, 3.8 Hz, 2H), 1.22 (s, 6H), 1.08 (s, 6H), 0.93 (apparent t, J=12.1 Hz, 2H).

Workup

  1. stirringthe reaction was stirred at 120° C. for 1 h
  2. customThe crude reaction mixture
  3. temperaturewas cooled to room temperature
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was recrystallized from CH3CN

Sources & evidence

ORD record
ord-98e36c326d0d4a5ea573365504bce52a
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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