Piperazin-1-ylpropanol → 4-(3-hydroxypropyl)-N-(6-methoxy-4-methyl-8-quinolinyl)-1-piperazinehexanamide

HRID 542835Notes

Reaction equation

HRID 542835 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][C:10]1[CH:11]=[C:12]([O:21][CH3:22])[CH:13]=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[C:15]2[CH3:20])=[O:8].[N:23]1([CH2:29][CH2:30][CH2:31][OH:32])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>C(OCC)(=O)C.C(N(CC)CC)C>[OH:32][CH2:31][CH2:30][CH2:29][N:23]1[CH2:28][CH2:27][N:26]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][C:10]2[CH:11]=[C:12]([O:21][CH3:22])[CH:13]=[C:14]3[C:19]=2[N:18]=[CH:17][CH:16]=[C:15]3[CH3:20])=[O:8])[CH2:25][CH2:24]1

Participants

5

Reactant 2

HCID 79207Piperazin-1-ylpropanolHCID 6120236-Bromo-N-(6-methoxy-4-methyl-8-quinolinyl)hexanamide

Product 1

HCID 202071744-(3-hydroxypropyl)-N-(6-methoxy-4-methyl-8-quinolinyl)-1-piperazinehexanamideYield 96%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4.3 g (0.012 mole) of 6-bromo-N-(6-methoxy-4-methyl-8-quinolinyl)hexanamide and 3.5 g (0.024 mole) of 1-piperazinepropanol was heated at 120° for 2 hr and allowed to cool. The mixture was diluted with ethyl acetate and excess triethylamine, washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to dryness to afford 4.9 g (96%) of the desired compound as a gum. The IR and NMR (CDCl3) were consistent with the assigned structure.

Workup

  1. temperaturewas heated at 120° for 2 hr
  2. temperatureto cool
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record
ord-d0fff633bbdf4e52882338496d65aa1e
Source dataset
uspto-grants-1987_04
Patent number
US04659708

Reaction notes

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