Benzylamine → 3-Benzylamino-6-(3-cyclopentyloxy-4-methoxyphenyl)pyridazine

HRID 2399354Notes

Reaction equation

HRID 2399354 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[CH:9]=2)=[CH:6][CH:7]=1.[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:22]([NH:29][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[CH:9]=2)=[CH:6][CH:7]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 193855003-Chloro-6-(3-cyclopentyloxy-4-methoxyphenyl)pyridazine

Product 1

HCID 193854833-Benzylamino-6-(3-cyclopentyloxy-4-methoxyphenyl)pyridazineYield 92.4%

Procedure

14 g (46 mmol) of 3-chloro-6-(3-cyclopentyloxy-4-methoxyphenyl)pyridazine are heated in 74 g (0.69 mol) of benzylamine at 200° C. for 3 hours. The mixture is subsequently poured onto ice and extracted with dichloromethane, and the organic phase is dried with potassium carbonate and then concentrated. Petroleum ether (b.p. 50°-70° C.) is added to the residue, and the resulting precipitate is filtered off with suction and crystallized from ethyl acetate/cyclohexane. 15.9 g (92.4%) of 3-benzylamino-6-(3-cyclopentyloxy-4-methoxyphenyl)pyridazine of m.p. 116° C. are obtained.

Workup

  1. additionThe mixture is subsequently poured onto ice
  2. extractionextracted with dichloromethane
  3. dry with materialthe organic phase is dried with potassium carbonate
  4. concentrationconcentrated
  5. additionPetroleum ether (b.p. 50°-70° C.) is added to the residue
  6. filtrationthe resulting precipitate is filtered off with suction
  7. customcrystallized from ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-9d574a73ca0645858722c352ff47eb81
Source dataset
uspto-grants-1995_09
Patent number
US05449676

Reaction notes

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