Diethylaminopropyl chloride, hydrochloride → HCID 20312118, compound

HRID 2420536Notes

Reaction equation

HRID 2420536 reaction equation
Cl.[CH2:2]([N:4]([CH2:9][CH3:10])[CH2:5][CH2:6][CH2:7]Cl)[CH3:3].[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[C:16]2[CH2:22][CH:23]1[NH:27][C:26](=[O:28])[NH:25][C:24]1=[O:29].[Na]>CN(C=O)C.C(O)C>[CH2:2]([N:4]([CH2:9][CH3:10])[CH2:5][CH2:6][CH2:7][N:25]1[C:24](=[O:29])[CH:23]([CH2:22][C:16]2[C:15]3[C:19](=[CH:20][CH:21]=[C:13]([O:12][CH3:11])[CH:14]=3)[NH:18][CH:17]=2)[NH:27][C:26]1=[O:28])[CH3:3]

Participants

6

Reactant 3

HCID 145749Diethylaminopropyl chloride, hydrochlorideHCID 5360545SodiumHCID 13653425HCID 13653425, compound

Product 1

HCID 20312118HCID 20312118, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

3-Diethylaminopropyl chloride hydrochloride (3.75 g, 0.024 mole) and a solution of 5-(5-methoxyindol-3-ylmethyl)hydantoin (6.1 g, 0.024 mole) in 100 ml of DMF were added to a solution of sodium (1.1 g) in 200 ml of anhydrous ethanol and the mixture was heated to reflux with stirring for 8 hours, filtered and concentrated in vacuo. The residue was recrystallized from aqueous methanol, yield 1.8 g, mp 136°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was recrystallized from aqueous methanol, yield 1.8 g, mp 136°

Sources & evidence

ORD record
ord-5cc302f6ec124247b4410e4dff2eb9ae
Source dataset
uspto-grants-1978_08
Patent number
US04110536

Reaction notes

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