Water → HCID 54029640, compound

HRID 2397580Notes

Reaction equation

HRID 2397580 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:6]3=[C:5]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:4]=2[CH:3]=1.[H-].[Na+].Cl[CH2:25][CH2:26][N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1.O>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][N:13]([CH2:25][CH2:26][N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)[C:14](=[O:15])[C:6]3=[C:5]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 816691-(2-Chloroethyl)pyrrolidineHCID 21436045HCID 21436045, compound

Product 1

HCID 54029640HCID 54029640, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
35 °C

Procedure

A solution of 8-chloro-10-phenyl-1,2,3,4-tetrahydropyrazino-[1,2-a]indole-1-one (6.0 g, 0.0202 mole) in dimethyl formamide (40 ml) is added over a period of 1/2 hour to a suspension of sodium hydride (1.4 g, 0.029 mole of a 50% dispersion in mineral oil) in dimethylformamide (20 ml). The mixture is stirred at about 35° C. for 1 hour. A solution of freshly distilled N-(β-chloroethyl)pyrrolidine (3.88 g, 0.029 mole) in dimethylformamide (10 ml) is added over a period of 1/4 hour. The reaction mixture is stirred at 50° C. for 18 hours, then cooled and poured into water (300 ml), this mixture is extracted with dichloromethane (4 portions, 100 ml each). The extracts are washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The drying agent is removed by filtration and the filtrate is concentrated. The residue is recrystallized from heptane to give the above titled product, 6.15 g (77.3 % yield), melting at 134°-135.5° C.

Workup

  1. stirringThe reaction mixture is stirred at 50° C. for 18 hours
  2. temperaturecooled
  3. extractionthis mixture is extracted with dichloromethane (4 portions, 100 ml each)
  4. washThe extracts are washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe drying agent is removed by filtration
  7. concentrationthe filtrate is concentrated
  8. customThe residue is recrystallized from heptane

Sources & evidence

ORD record
ord-2053cf94046a41c0b0cf3f3c0f62a02d
Source dataset
uspto-grants-1977_05
Patent number
US04022778

Reaction notes

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