Phenol → HCID 23355235, compound

HRID 234684Notes

Reaction equation

HRID 234684 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:13][C:14]([N:18]1CCCCC1)([CH3:17])[CH2:15][NH2:16].[C:24]1(O)[CH:29]=[CH:28][CH:27]=[CH:26]C=1>>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:18][C:14]([CH3:17])([CH3:13])[CH2:15][N:16]3[CH2:26][CH2:27][CH2:28][CH2:29][CH2:24]3)=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 68664,7-DichloroquinolineHCID 17131181-(2-Amino-1,1-dimethylethyl)piperidine

Product 1

HCID 23355235HCID 23355235, compoundYield 31.6%

Procedure

4.57 g of 4,7-dichloroquinoline, 7.5 g of 2-methyl-2-(piperidin-1-yl)-propylamine and 0.75 g of phenol were reacted at 180° C. for 16 hours. The crude reaction product, isolated as in the preceeding Example, was purified on 200 g of aluminium oxide (activity grade II) prior to recrystallization; a 1:1 mixture of toluene and acetone was used as the eluent. After a fore-run, which contained unreacted 4,7-dichloroquinoline, the product was eluted and, after recrystallization from 5 ml of acetonitrile, yielded 0.8 g of colourless crystals, m.p.: 143°-147° C.

Workup

  1. customThe crude reaction product
  2. customwas purified on 200 g of aluminium oxide (activity grade II)
  3. customto recrystallization
  4. additiona 1:1 mixture of toluene and acetone
  5. washthe product was eluted
  6. customafter recrystallization from 5 ml of acetonitrile

Sources & evidence

ORD record
ord-9a09b32cb1054981bb27fa8a71fade94
Source dataset
uspto-grants-1997_01
Patent number
US05596002

Reaction notes

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