Chloroacetyl chloride → HCID 21446147, compound

HRID 597737Notes

Reaction equation

HRID 597737 reaction equation
C([O-])(=O)C.[Na+].[NH:6]1[CH2:11][CH2:10][CH2:9][C:8]2([CH2:16][CH:15]3[CH2:17][CH2:18][CH:12]2[CH2:13][CH2:14]3)[CH2:7]1.[Cl:19][CH2:20][C:21](Cl)=[O:22]>O.CC(C)=O>[Cl:19][CH2:20][C:21]([N:6]1[CH2:11][CH2:10][CH2:9][C:8]2([CH2:16][CH:15]3[CH2:17][CH2:18][CH:12]2[CH2:13][CH2:14]3)[CH2:7]1)=[O:22]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 517045Sodium AcetateHCID 21446145HCID 21446145, compound

Product 1

HCID 21446147HCID 21446147, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

An amount of 20 g (0.244 mole) of sodium acetate and 18 g (0.100 mole) of spiro[bicyclo[2.2.2]octane2,3'-piperidine] is dissolved in 100 ml of water and 300 ml of acetone. A two-phase system is formed, to which is added dropwise at 0° to 5° an amount of 10.2 ml (14.4 g, 0.13 mole) of chloroacetyl chloride. An addition is then made to the mixture, at 0° to 5°, of 700 ml of water, whereupon the reaction product precipitates in flake form. Stirring is maintained for a further hour and the reaction product subsequently filtered off. After washing and then drying of the product over phosphorus pentoxide in a desiccator, there is obtained 1'-chloroacetyl-spiro [bicyclo[2.2.2]octane-2,3'-piperidine], M.P. 63° (with decomposition).

Workup

  1. customA two-phase system is formed, to which
  2. additionAn addition
  3. customprecipitates in flake form
  4. temperatureis maintained for a further hour
  5. filtrationthe reaction product subsequently filtered off
  6. washAfter washing
  7. dry with materialdrying of the product over phosphorus pentoxide in a desiccator

Sources & evidence

ORD record
ord-7fd8e2b26a074a268e553ff97d3b337a
Source dataset
uspto-grants-1977_03
Patent number
US04015007

Reaction notes

Loading…