Chloroacetyl chloride → HCID 68121302, compound

HRID 2397578Notes

Reaction equation

HRID 2397578 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[Cl:6][C:7]1[CH:15]=[CH:14][C:13]2[N:12]3[CH2:16][CH2:17][NH:18][CH2:19][C:11]3=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:9]=2[CH:8]=1.C([N:28](CC)CC)C>ClCCl>[Cl:1][CH2:2][C:3]([NH:28][CH:19]1[C:11]2=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:9]3[CH:8]=[C:7]([Cl:6])[CH:15]=[CH:14][C:13]=3[N:12]2[CH2:16][CH2:17][NH:18]1)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 15733250HCID 15733250, compound

Product 1

HCID 68121302HCID 68121302, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
39 °C

Procedure

A solution of chloracetyl chloride (4.60 g, 0.0407 mole) in dichloromethane (25 ml) is added over a period of three-fourth hours to a solution of 8chloro-10-phenyl-1,2,3,4-tetrahydropyrazino[1,2-a] indole (10.0 g, 0.0353 mole) and triethylamine (4.13 g, 0.0407 mole) in dichloromethane (100 ml). An exotherm raises the temperature to 39° C. The reaction mixture is stirred at room temperature for 6 hours, then allowed to stand overnight. It is concentrated to dryness. The residue was taken up in dichloromethane (500 ml), washed with water and saturated sodium chloride solution and dried over anhydrous sodium sulfate. The drying agent is removed by filtration and the filtrate is concentrated to dryness. The residue is recrystallized twice from isopropanol, giving the above titled product, 6.94 g (54.7% yield), melting at 139°-149° C.

Workup

  1. waitto stand overnight
  2. concentrationIt is concentrated to dryness
  3. washwashed with water and saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe drying agent is removed by filtration
  6. concentrationthe filtrate is concentrated to dryness
  7. customThe residue is recrystallized twice from isopropanol

Sources & evidence

ORD record
ord-c51b1a2454ac4dff82a03d94fe86a711
Source dataset
uspto-grants-1977_05
Patent number
US04022778

Reaction notes

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