Piperazine → HCID 11201996, compound

HRID 2217841Notes

Reaction equation

HRID 2217841 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8]([C:12]([NH:14][CH2:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:13])=[C:7]([Cl:22])[CH:6]=[CH:5][C:4]=2[N:3]=1.[NH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>C(#N)C>[ClH:1].[ClH:1].[Cl:22][C:7]1[CH:6]=[CH:5][C:4]2[N:3]=[C:2]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[CH:11]=[CH:10][C:9]=2[C:8]=1[C:12]([NH:14][CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:13]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 860130222,6-dichloro-N-(cyclohexylmethyl)-5-quinolinecarboxamide

Product 1

HCID 11201996HCID 11201996, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of 2,6-dichloro-N-(cyclohexylmethyl)quinoline-5-carboxamide (Example 43 (a)) (200 mg) and piperazine (160 mg) in acetonitrile (2 mL) was heated at 80° C. in a CEM Discover microwave for 1 hour after which it was cooled to room temperature and concentrated. The residue was purified (Waters' SCX resin, ammonia in methanol (7 M) as eluant) and the resultant product was converted to the dihydrochloride salt by treatment with hydrochloric acid (4M in 1,4-dioxane). Recrystallisation (methanol/ethyl acetate) afforded the title compound as a solid (110 mg).

Workup

  1. customwas heated at 80° C. in a CEM Discover microwave for 1 hour
  2. concentrationconcentrated
  3. customThe residue was purified (Waters' SCX resin, ammonia in methanol (7 M) as eluant)
  4. customRecrystallisation (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-8fe27363cd784db28322b139749aeb9b
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

Loading…