Diethylaminopropyl chloride, hydrochloride → HCID 20312101, compound

HRID 2420533Notes

Reaction equation

HRID 2420533 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[NH:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:2]1.[Na].Cl.[CH2:19]([N:21]([CH2:26][CH3:27])[CH2:22][CH2:23][CH2:24]Cl)[CH3:20]>CN(C=O)C.C(O)C>[CH2:19]([N:21]([CH2:26][CH3:27])[CH2:22][CH2:23][CH2:24][N:12]1[C:11](=[O:16])[CH:10]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[NH:14][C:13]1=[O:15])[CH3:20]

Participants

6

Reactant 3

HCID 145749Diethylaminopropyl chloride, hydrochlorideHCID 5360545SodiumHCID 20186934HCID 20186934, compound

Product 1

HCID 20312101HCID 20312101, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(indol-3-yl)hydantoin (5.2 g, 0.024 mole) in 100 ml of DMF was added to a solution of sodium (1.1 g) in 100 ml of anhydrous C2H5OH. The solution was warmed warmed 3-diethylaminopropyl chloride hydrochloride (4.5 g, 0.024 mole) was added and the mixture was heated to reflux with stirring for 18 hours, filtered and diluted with H2O. The crude free base (2.5 g) and oxalic acid (1.5 g) was dissolved in methanol and diluted with ethyl acetate. The solid was collected and dried, yield 1.0 g, mp 231°-2°.

Workup

  1. temperatureThe solution was warmed
  2. additionwas added
  3. temperaturethe mixture was heated
  4. temperatureto reflux
  5. filtrationfiltered
  6. additiondiluted with H2O
  7. dissolutionThe crude free base (2.5 g) and oxalic acid (1.5 g) was dissolved in methanol
  8. additiondiluted with ethyl acetate
  9. customThe solid was collected
  10. customdried

Sources & evidence

ORD record
ord-ecfb866d4c014cafab2f947fd987af3b
Source dataset
uspto-grants-1978_08
Patent number
US04110536

Reaction notes

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