4-Chlorobenzoyl chloride → HCID 131711511, compound

HRID 1389250Notes

Reaction equation

HRID 1389250 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[C:5]([CH2:19][NH:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:4]=1.[Cl:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1>C(Cl)(Cl)Cl>[ClH:29].[Cl:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([N:20]([CH2:19][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:18]=[CH:17][C:6]=2[O:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:35])=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 20298675HCID 20298675, compound

Product 1

HCID 131711511HCID 131711511, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 16.0 g. of 4-[3-[4-methoxy-2-[[(2-phenylethyl)amino]methyl]phenoxy]propyl]morpholine in 50 ml. of chloroform is added dropwise (at 10°-15° C.) to a stirred solution of 7.7 g of p-chlorobenzoyl chloride in 150 ml. of chloroform. After the addition is completed, the solution is stirred at room temperature for 2 hours, heated at reflux for 1 hour, cooled and concentrated to give a glass-like residue. The residue is rubbed under ether, the evaporation repeated and the partly solid residue taken up in 100 ml of acetonitrile. On diluting to 650 ml with ether, seeding and rubbing, the crystalline hydrogen chloride salt separates. After cooling overnight, the product weighs 21.7 g, melting point 137°-139° C. Recrystallization from 50 ml of warm acetonitrile-50 ml of ether, yields 20.3 g of the title compound, melting point 138°-140° C.

Workup

  1. additionAfter the addition
  2. temperatureheated
  3. temperatureat reflux for 1 hour
  4. temperaturecooled
  5. concentrationconcentrated
  6. customto give a glass-like residue
  7. customthe evaporation
  8. additionOn diluting to 650 ml with ether
  9. temperatureAfter cooling overnight
  10. customRecrystallization from 50 ml of warm acetonitrile-50 ml of ether

Sources & evidence

ORD record
ord-9bb56ec81a60420ba0457a3680a5c046
Source dataset
uspto-grants-1981_01
Patent number
US04243804

Reaction notes

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