Diethylaminopropyl chloride, hydrochloride → 3-(3-Diethylaminopropyl)-5-(indol-3-ylmethyl)hydantoin

HRID 2420534

Reaction equation

HRID 2420534 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.Cl.Cl[CH2:20][CH2:21][CH2:22][N:23]([CH2:26][CH3:27])[CH2:24][CH3:25].CC[O-].[Na+]>C(O)C>[CH2:24]([N:23]([CH2:26][CH3:27])[CH2:22][CH2:21][CH2:20][N:13]1[C:12](=[O:17])[CH:11]([CH2:10][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[NH:15][C:14]1=[O:16])[CH3:25]

Participants

5

Reactant 3

HCID 145749Diethylaminopropyl chloride, hydrochlorideHCID 2428675-(1h-Indol-3-ylmethyl)imidazolidine-2,4-dioneHCID 2723922Sodium ethoxide

Product 1

HCID 203121193-(3-Diethylaminopropyl)-5-(indol-3-ylmethyl)hydantoin

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(indol-3-ylmethyl)hydantoin (10 g, 0.04 mole), 3-chloro-N,N-diethylpropylamine hydrochloride (8.2 g, 0.04 mole), NaOC2H5 (0.08 mole) and 500 ml of anhydrous C2H5OH was heated to reflux with stirring for 20 hours. The mixture was filtered and concentrated to dryness. The concentrate was dissolved in CHCl3, filtered and concentrated. The concentrate was crystallized and recrystallized from benzene-petroleum ether. The solid was again recrystallized from xylene and the solvated solid was dried in vacuum, yield 2.5 g, mp 90°.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated to dryness
  5. dissolutionThe concentrate was dissolved in CHCl3
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe concentrate was crystallized
  9. customrecrystallized from benzene-petroleum ether
  10. customThe solid was again recrystallized from xylene
  11. customthe solvated solid was dried in vacuum, yield 2.5 g, mp 90°

Sources & evidence

ORD record
ord-9fac1453dee7497da7051b9ae27155c3
Source dataset
uspto-grants-1978_08
Patent number
US04110536

Linked notes

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