Chloroacetyl chloride → HCID 21832634, compound

HRID 266011Notes

Reaction equation

HRID 266011 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C([N:10](CC)CC)C.[Cl:15][CH2:16][C:17](Cl)=[O:18]>C(Cl)(Cl)Cl>[Cl:15][CH2:16][C:17]([NH2:1])=[O:18].[Cl:15][CH2:16][C:17]([NH2:10])=[O:18].[NH:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 68163Hexahydro-1,4-diazepine

Product 1

HCID 21832634HCID 21832634, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
-30 °C

Procedure

Homopiperazine (10 g; 100 mmol) was dissolved in chloroform (150 mL) and triethylamine (28 mL; 500 mmol) was added to the mixture. The solution was cooled to -30° C. under nitrogen and chloroacetyl chloride (17 mL, 213 mmol) was added over a period of 1 hour. The solution was stirred at -30° C. for 1 hour, at 0° C. for 2 hour and at ambient temperature overnight. The solution was washed with water (4×50 mL), dried over anhydrous MgSO4, filtered and concentrated. The oily residue was purified by column chromatography on silica gel (5% methanol in chloroform) to yield the title product as an oil which solidified on prolonged standing (10.3 g; 41%). 1H NMR (CDCl3): 4.04 (m, 4 H), 3.62 (m, 8 H), and 1.94 (m, 2H).

Workup

  1. washThe solution was washed with water (4×50 mL)
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe oily residue was purified by column chromatography on silica gel (5% methanol in chloroform)

Sources & evidence

ORD record
ord-a90b1cbf3cc8419e90aadadb461cb763
Source dataset
uspto-grants-1997_07
Patent number
US05650133

Reaction notes

Loading…