Benzene → HCID 53964454, compound

HRID 1709634Notes

Reaction equation

HRID 1709634 reaction equation
[C:1]([CH2:9][CH2:10][C:11]([OH:13])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC=CC=1.ClC(OCC)=O.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.C([N:34](CC)CC)C>>[N:26]1([NH:34][C:11](=[O:13])[CH2:10][CH2:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1

Participants

6

Reactant 5

HCID 241BenzeneHCID 8083MorpholineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 728713-Benzoylpropionic acid

Product 1

HCID 53964454HCID 53964454, compoundYield 57.2%

Procedure

A suspension of 17.8 grams (0.1 mole) of β-benzoyl-propionic acid (Organic Synthesis, 2:81) in 500 milliters of dry benzene is prepared and 10.5 grams of triethylamine, 15 grams of ethyl chloroformate, and 18 grams (0.2 mole) of morpholine are sequentially added. The suspension is stirred for two hours at room temperature and then filtered to remove the precipitated triethylamine hydrochloride. The mother liquor is evaporated in a small amount for filtration and the solid product which is obtained, is separated by filtration and crystallized from ethanol to provide about 15 grams of N-morpholinyl-β-benzoyl-propionamide having a melting point of 87°-89° C.

Workup

  1. customis prepared
  2. filtrationfiltered
  3. customto remove the precipitated triethylamine hydrochloride
  4. customThe mother liquor is evaporated in a small amount for filtration
  5. customthe solid product which is obtained
  6. customis separated by filtration
  7. customcrystallized from ethanol

Sources & evidence

ORD record
ord-12039987fe8c4d04894e7aa8088203eb
Source dataset
uspto-grants-1990_08
Patent number
US04950669

Reaction notes

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