5-(1h-Indol-3-ylmethyl)imidazolidine-2,4-dione → 5-[(Indol-3-yl)methyl]-3-(3-morpholinopropyl)hydantoin

HRID 2420530

Reaction equation

HRID 2420530 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]2[NH:15][C:14](=[O:16])[NH:13][C:12]2=[O:17])=[CH:2]1.[CH3:18][CH2:19][O-:20].[Na+]>C(O)C.O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]2[NH:15][C:14](=[O:16])[N:13]([CH2:4][CH2:3][CH2:2][N:1]3[CH2:9][CH2:8][O:20][CH2:19][CH2:18]3)[C:12]2=[O:17])=[CH:2]1

Participants

5

Reactant 2

HCID 2428675-(1h-Indol-3-ylmethyl)imidazolidine-2,4-dioneHCID 2723922Sodium ethoxide

Product 1

HCID 203121155-[(Indol-3-yl)methyl]-3-(3-morpholinopropyl)hydantoin

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

5-[(Indol-3-yl)methyl]hydantoin (5 g; 0.022 mole) was added to NaOC2H5 (0.022 mole) in 300 ml of anhydrous C2H5OH. The first mixture was heated to reflux, and 1-(3-chloropropyl)-morpholine (3.5 g, 0.022 mole) was added. The mixture was heated for 6 hours and then diluted with H2O. The solid was collected and recrystallized from 2-propanol-petroleum ether, yield 3 g, mp 158°-60°.

Workup

  1. temperatureThe first mixture was heated
  2. temperatureto reflux
  3. temperatureThe mixture was heated for 6 hours
  4. customThe solid was collected
  5. customrecrystallized from 2-propanol-petroleum ether, yield 3 g, mp 158°-60°

Sources & evidence

ORD record
ord-fc4cb6b5a44f4c1c8f3999b6c49a33b3
Source dataset
uspto-grants-1978_08
Patent number
US04110536

Linked notes

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