Chloroacetyl chloride → HCID 86737798, compound

HRID 1680501Notes

Reaction equation

HRID 1680501 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH2:6]1[CH:11]2[C:12]3[C:17]([C:18](=[O:19])[N:10]2[CH2:9][CH2:8][NH:7]1)=[CH:16][CH:15]=[CH:14][CH:13]=3.C(N(CC)CC)C>C1C=CC=CC=1>[Cl:1][CH2:2][C:3]([CH:6]1[CH:11]2[C:12]3[C:17]([C:18](=[O:19])[N:10]2[CH2:9][CH2:8][NH:7]1)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 12901777HCID 12901777, compound

Product 1

HCID 86737798HCID 86737798, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of chloroacetyl chloride (657 mg, 0.0058 mol) in 30 ml of benzene is added dropwise to a stirring solution of 1,2,3,4,6,10b-hexahydropyrazino[2,1-a]isoindole-6-one (described in Example 8, 1.0 g, 0.0053 mol) and triethylamine (650 mg, 0.0064 mol) in 90 ml of benzene. The reaction is stirred at room temperature for 30 min and evaporated. A mixture of chloroform and water is added and the chloroform phase is collected, washed with water, dried and evaporated to afford 2-chloroacetyl-1,2,3,4,6,10b-hexahydropyrazino[2,1-a]isoindole-6-one, (1.2 g), nmr (CDCl3) δ 3.0-3.5(m), 4.2-4.8(m) and 7.3-7.9(m).

Workup

  1. customevaporated
  2. additionA mixture of chloroform and water
  3. additionis added
  4. customthe chloroform phase is collected
  5. washwashed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-3909de2b8b5542099651b90443247909
Source dataset
uspto-grants-1981_06
Patent number
US04273773

Reaction notes

Loading…