4-Benzylpiperidine → HCID 11993597, compound

HRID 2266320Notes

Reaction equation

HRID 2266320 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[CH:10][C:11]2[N:12]([C:14]([C:17](OCC)=[O:18])=[N:15][N:16]=2)[N:13]=1.[CH2:29]([CH:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CO>[CH2:29]([CH:36]1[CH2:41][CH2:40][N:39]([C:17]([C:14]2[N:12]3[N:13]=[C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[C:9]([C:22]4[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=4)=[CH:10][C:11]3=[N:16][N:15]=2)=[O:18])[CH2:38][CH2:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 317384-BenzylpiperidineHCID 11993498HCID 11993498, compound

Product 1

HCID 11993597HCID 11993597, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 6-(2-chlorophenyl)-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine-3-carboxylate (21 mg, 0.05 mmol) and 4-benzylpiperidine (0.175 mL, 1.0 mmol) in methanol (0.5 mL) was heated in a microwave oven at 160° C. for 30 min. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure, then the crude product was purified using reverse phase preparative HPLC (Conditions: Water SunFire Prep C18, OBD 19×100 m, 5 □m; Fluted with 0% to 100% B, 10 min gradient, 100% B hold for 5 min, (A 90% H2O, 10% MeOH, 0.1% of TEA and B 10% H2O, 90% MeOH, 0.1% of TFA); Flow rate at 20 mL/min, UV detection at 220 nm) to afford 18 mg (66%) of the title compound as a white powder. HPLC/MS (method A): retention time=4.12 min, (M+H)+=542.1.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe crude product was purified

Sources & evidence

ORD record
ord-7985d932178a472781c4d0c96d6a1b27
Source dataset
uspto-grants-2010_12
Patent number
US07858639B2

Reaction notes

Loading…