Morpholine → HCID 13375756, compound

HRID 745863Notes

Reaction equation

HRID 745863 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[CH2:8][C:9]([NH:11][C:12]1[CH:21]=[C:20]2[C:15]([C:16](=[O:35])[C:17]([CH2:32][CH2:33][CH3:34])=[C:18]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:23]=3)[O:19]2)=[CH:14][CH:13]=1)=[O:10]>C1C=CC=CC=1>[O:4]1[CH2:5][CH2:6][N:1]([CH2:8][C:9]([NH:11][C:12]2[CH:21]=[C:20]3[C:15]([C:16](=[O:35])[C:17]([CH2:32][CH2:33][CH3:34])=[C:18]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:23]=4)[O:19]3)=[CH:14][CH:13]=2)=[O:10])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 13375745HCID 13375745, compound

Product 1

HCID 13375756HCID 13375756, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The mixture consisting of 9.2 of this derivative, 700 cc of benzene, 20 cc of morpholine is heated to reflux of the benzene with stirring for 4 hours, then cooled. The benzene phase is washed with water several times, dried on sodium sulfate and evaporated. The residue is recrystallized in ethyl alcohol. Yield 60%. MP=196° C. NMR in CDCl3 : δ=0.9 ppm, 3H, triplet, CH3 (propyl), δ=1.2-1.9 ppm, 2H, poorly resolved multiplet, CH2CH2CH3 ; δ=2.3-2.9 ppm, 6H, complex multiplet, CH2CH2CH3 +2CH2N (morpholine); δ=3.2 ppm, 2H, singlet, COCH2N; δ=4.0 ppm, 3H, singlet, CH3, ester; δ=7.0-8.3 ppm, 7H, complex multiplet, aromatic protons; δ=9.4 ppm, 1H, broad peak, NH, (interchangeable with D2O).

Workup

  1. temperatureis heated
  2. temperaturecooled
  3. washThe benzene phase is washed with water several times
  4. customdried on sodium sulfate
  5. customevaporated
  6. customThe residue is recrystallized in ethyl alcohol

Sources & evidence

ORD record
ord-0c5bd013bd334700926717ee18970200
Source dataset
uspto-grants-1986_07
Patent number
US04600788

Reaction notes

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