Sodium Iodide → HCID 86736121, compound

HRID 1863097Notes

Reaction equation

HRID 1863097 reaction equation
[Cl:1]CCC[N:5](C)C(=O)C(C1C=CC(Cl)=CC=1CC1C=CC=CC=1)=O.[I-].[Na+].N1CCOCC1.Cl.[O:34]1[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][CH2:42][N:43]([CH3:63])[C:44](=[O:62])[C:45]([C:47]2[CH:52]=[CH:51][C:50]([Cl:53])=[CH:49][C:48]=2[C:54](=O)[C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=O)[CH2:36][CH2:35]1>CC(CC)=O>[ClH:1].[O:34]1[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][CH2:42][N:43]([CH3:63])[C:44]([C:45]2[NH:5][C:54]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)=[C:48]3[C:47]=2[CH:52]=[CH:51][C:50]([Cl:53])=[CH:49]3)=[O:62])[CH2:36][CH2:35]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8083MorpholineHCID 54028532HCID 54028532, compoundHCID 86736122HCID 86736122, compound

Product 1

HCID 86736121HCID 86736121, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 7.6 g. of o-benzyl-p-chlorophenylglyoxylic acid (3-chloropropyl)methylamide in 40 ml. of ethyl methyl ketone is treated with 3.0 g. of sodium iodide and 3.5 g. of morpholine and the mixture is boiled at reflux for 30 hours. After concentration under reduced pressure, the residue is partitioned between water and methylene chloride, the organic phase washed with water, dried over sodium sulfate and concentrated to dryness. The residual oily base is purified on 500 g. of aluminum oxide using methylene chloride/ethyl acetate (4:1) for the elution, dissolved in diethyl ether and treated with excess ethereal hydrochloric acid. The hydrochloride which crystallizes out is recrystallized from isopropanol/diethyl ether, and there is obtained 4.9 g. of o-benzoyl-p-chlorophenylglyoxylic acid [3-(morpholino)propyl]methylamide hydrochloride in the form of light yellow crystals having a melting point of 169°-172° C. (decomposition).

Workup

  1. temperatureat reflux for 30 hours
  2. concentrationAfter concentration under reduced pressure
  3. customthe residue is partitioned between water and methylene chloride
  4. washthe organic phase washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to dryness
  7. customThe residual oily base is purified on 500 g
  8. washfor the elution
  9. dissolutiondissolved in diethyl ether
  10. additiontreated with excess ethereal hydrochloric acid
  11. customThe hydrochloride which crystallizes out
  12. customis recrystallized from isopropanol/diethyl ether
  13. customthere is obtained 4.9 g

Sources & evidence

ORD record
ord-08b91221002c476fbeb0873f12375c78
Source dataset
uspto-grants-1979_09
Patent number
US04167632

Reaction notes

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