Ethanol → 8-Chloro-2-(diethylaminoacetyl)-1,2,3,4-tetrahydro-10-phenylpyrazino[1,2-a]indole

HRID 2397579Notes

Reaction equation

HRID 2397579 reaction equation
Cl[CH2:2][C:3]([NH:5][CH:6]1[C:11]2=[C:12]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:13]3[CH:14]=[C:15]([Cl:19])[CH:16]=[CH:17][C:18]=3[N:10]2[CH2:9]CN1)=[O:4].[CH2:26]([NH:28][CH2:29][CH3:30])[CH3:27].[I-].[Na+].[CH2:33](O)C>>[Cl:19][C:15]1[CH:16]=[CH:17][C:18]2[N:10]3[CH2:9][CH2:33][N:5]([C:3](=[O:4])[CH2:2][N:28]([CH2:29][CH3:30])[CH2:26][CH3:27])[CH2:6][C:11]3=[C:12]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:13]=2[CH:14]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 5238Sodium IodideHCID 8021DiethylamineHCID 68121302HCID 68121302, compound

Product 1

HCID 214360468-Chloro-2-(diethylaminoacetyl)-1,2,3,4-tetrahydro-10-phenylpyrazino[1,2-a]indoleYield 70.9%

Procedure

A mixture of 2-chloroacetamido-8-chloro-10-phenyl-1,2,3,4-tetrahydropyrazino[1,2-a]indole (6.80 g, 0.0189 mole), diethylamine (3.46 g, 0.0473 mole) and sodium iodide (2.85 g, 0.019 mole) in ethanol (250 ml) is refluxed for 10 hours, then cooled to room temperature. The solid is removed by filtration and the filtrate is concentrated. The residue is taken up in dichloromethane (350 ml) and extracted with 10% hydrochloric acid (300 ml) in 4 portions. The dichloromethane solution is concentrated to a brown gummy residue. This is extracted with boiling water (500 ml), filtering off the insoluble material. The aqueous solution is basified to pH 10 with excess solid potassium carbonate. A solid is formed which is collected by filtration and is recrystallized from heptane to give the above titled product, 5.30 g (70.9% yield) melting at 117°-119° C.

Workup

  1. temperatureis refluxed for 10 hours
  2. customThe solid is removed by filtration
  3. concentrationthe filtrate is concentrated
  4. extractionextracted with 10% hydrochloric acid (300 ml) in 4 portions
  5. concentrationThe dichloromethane solution is concentrated to a brown gummy residue
  6. extractionThis is extracted with boiling water (500 ml)
  7. filtrationfiltering off the insoluble material
  8. customA solid is formed which
  9. filtrationis collected by filtration
  10. customis recrystallized from heptane

Sources & evidence

ORD record
ord-5be7ddeb91704971b60b978b03992e0b
Source dataset
uspto-grants-1977_05
Patent number
US04022778

Reaction notes

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