Benzoyl chloride → HCID 20062708, compound

HRID 1084751Notes

Reaction equation

HRID 1084751 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][CH2:12][C:13]2[CH:14]=[C:15]([CH:19]([OH:24])[CH2:20][CH2:21][CH2:22][CH3:23])[CH:16]=[CH:17][CH:18]=2)[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:32](Cl)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>ClCCl>[C:32]([O:24][CH:19]([C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([CH2:12][O:11][C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[N:1]=[CH:2][CH:3]=[CH:4]3)[CH:14]=1)[CH2:20][CH2:21][CH2:22][CH3:23])(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 20062665HCID 20062665, compound

Product 1

HCID 20062708HCID 20062708, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

3.2 g (10 mmol) of 1-[3-(quinolin-8-yloxymethyl)phenyl]-pentanol are dissolved in 50 ml of dichloromethane. After the addition of 2.8 ml of triethylamine and 1.16 ml of benzoyl chloride, the mixture is stirred for 2 hours at 25° C. and then heated under reflux for 5 hours. The reaction mixture is washed three times with water, dried over sodium sulphate and evaporated down. The residue is chromatographed over silica gel 60 (mobile phase: 100:2 dichloromethane/methanol). An oil is obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. washThe reaction mixture is washed three times with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated down
  6. customThe residue is chromatographed over silica gel 60 (mobile phase: 100:2 dichloromethane/methanol)
  7. customAn oil is obtained

Sources & evidence

ORD record
ord-1d70e89b5bb64f0faa1b615d1696abcb
Source dataset
uspto-grants-1991_04
Patent number
US05006534

Reaction notes

Loading…