Benzyl Alcohol → HCID 44176641, compound

HRID 657529Notes

Reaction equation

HRID 657529 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:12]1[N:13]=[N:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:20][CH:19]=2)=[CH:16][CH:17]=1>CN(C=O)C>[CH2:3]([O:10][C:12]1[N:13]=[N:14][C:15]([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:22][CH:23]=2)=[CH:16][CH:17]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 44178184HCID 44178184, compound

Product 1

HCID 44176641HCID 44176641, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.007 g, 0.18 mmol) was stirred in anhydrous DMF (4 mL) under a nitrogen atmosphere, and benzyl alcohol (0.016 g, 0.15 mmol) was added. After 15 min., 3-chloro-6-[4-(3-piperidin-1-yl-propoxy)-phenyl]-pyridazine (0.05 g, 0.15 mmol) was introduced, and the reaction mixture was stirred at room temperature for 5 h. The precipitate was collected by filtration, washed with H2O (10 mL) and dried in vacuo to provide the title compound as a white solid (0.050 g, 83%), m.p. 138° C.; 1H NMR (CDCl3) 2.00 (m, 2H, —CH2—), 2.50 (m, 2H, —CH2—), 4.10 (m, 2H, —CH2—), 7.00 (d, 1H, C—H), 7.05 (d, 2H, Ar—H), 7.75 (d, 1H, C—H), 7.95 (d, 2H, Ar—H) HPLC retention time 2.612 mina.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with H2O (10 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-1528772dfa104e1b819e3e2997cf065f
Source dataset
uspto-grants-2011_12
Patent number
US08076331B2

Reaction notes

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