Diethylaminopropyl chloride, hydrochloride → HCID 70625011, compound

HRID 2420535Notes

Reaction equation

HRID 2420535 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH:12]1[NH:16][C:15](=[O:17])[NH:14][C:13]1=[O:18].[Na].Cl.[CH2:21]([N:23]([CH2:28][CH3:29])[CH2:24][CH2:25][CH2:26]Cl)[CH3:22]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH:12]1[NH:16][C:15](=[O:17])[N:14]([CH2:26][CH2:25][CH2:24][N:23]([CH2:28][CH3:29])[CH2:21][CH3:22])[C:13]1=[O:18]

Participants

5

Reactant 3

HCID 145749Diethylaminopropyl chloride, hydrochlorideHCID 5360545SodiumHCID 20312104HCID 20312104, compound

Product 1

HCID 70625011HCID 70625011, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(5-Chloroindol-3-ylmethyl)hydantoin (5 g, 0.019 mole) was added to a solution of sodium (0.88 g) in 200 ml of anhydrous C2H5OH. After heating to reflux for 30 minutes, 3-diethylaminopropyl chloride hydrochloride (3.54 g, 0.019 mole) was added and the mixture was heated to reflux with stirring for 18 hours. The mixture was filtered and diluted with H2O to form a solid. The solid was recrystallized from aqueous 2-propanol, twice from acetone-petroleum ether and again from 2-propanol, yield 1.8 g, mp 186°.

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for 30 minutes
  3. temperaturethe mixture was heated
  4. temperatureto reflux
  5. filtrationThe mixture was filtered
  6. additiondiluted with H2O
  7. customto form a solid
  8. customThe solid was recrystallized from aqueous 2-propanol, twice from acetone-petroleum ether and again from 2-propanol, yield 1.8 g, mp 186°

Sources & evidence

ORD record
ord-6d3ebabc4d25412aaee96eef80aaf694
Source dataset
uspto-grants-1978_08
Patent number
US04110536

Reaction notes

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