Potassium Carbonate → HCID 22122084, compound

HRID 1858938Notes

Reaction equation

HRID 1858938 reaction equation
Cl[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH2:25][CH2:24][CH:23]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[CH2:22][CH:21]=2)=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>>[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH2:25][CH2:24][CH:23]([N:26]3[CH2:27][CH2:28][N:29]([CH2:2][C:3]4[CH:12]=[CH:11][C:10]5[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=5)[N:4]=4)[CH2:30][CH2:31]3)[CH2:22][CH:21]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 22122096HCID 22122096, compound

Product 1

HCID 22122084HCID 22122084, compoundYield 53%

Procedure

A mixture of 2-chloromethylquinoline (4.7 mmole), and 1-[4-(4-fluorophenyl)-3-cyclohexen-1-yl]piperazine (4.7 mmole) and excess powdered K2CO3 was heated at reflux for 18 hr. The insolubles were removed by filtration, the solution concentrated in vacuo, and the residue crystallized from hexane to give the product (53%, mp: 111-114° C.). Calc'd for C26H28FN3: C, 77.78%; H, 7.03%; N, 10.47%. Found: C, 77.61; H, 6.91%; N, 10.72%.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hr
  3. customThe insolubles were removed by filtration
  4. concentrationthe solution concentrated in vacuo
  5. customthe residue crystallized from hexane

Sources & evidence

ORD record
ord-fd2b9c83fbb747b58efcb5a289e44841
Source dataset
uspto-grants-2000_11
Patent number
US06153611

Reaction notes

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