3-Chloropropionyl chloride → HCID 21446167, compound

HRID 597738Notes

Reaction equation

HRID 597738 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C:3]2([CH2:11][CH:10]3[CH2:12][CH2:13][CH:7]2[CH2:8][CH2:9]3)[CH2:2]1.C([O-])(=O)C.[Na+].[Cl:19][CH2:20][CH2:21][C:22](Cl)=[O:23]>CC(C)=O.O>[Cl:19][CH2:20][CH2:21][C:22]([N:1]1[CH2:6][CH2:5][CH2:4][C:3]2([CH2:11][CH:10]3[CH2:12][CH2:13][CH:7]2[CH2:8][CH2:9]3)[CH2:2]1)=[O:23]

Participants

6

Reactant 3

HCID 693643-Chloropropionyl chlorideHCID 517045Sodium AcetateHCID 21446145HCID 21446145, compound

Product 1

HCID 21446167HCID 21446167, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

An amount of 2.0 g (0.0112 mole) of spiro[bicyclo [2.2.2]octane-2,3'-piperidine] is added, with ice cooling and with stirring, to a suspension of 2.4 g of sodium acetate in 30 ml of acetone and 10 ml of water; there is then added dropwise to the formed mixture at 0°-5° 1.8 g (0.014 mole) of 3-chloropropionyl chloride. An addition is subsequently made to the mixture, at 0°-5°, of 70 ml of water, whereupon the reaction product precipitates in liquid form. The mixture is extracted three times with 50 ml of methylene chloride each time. The methylene chloride extracts are washed separately in each case once with saturated sodium bicarbonate solution and twice with water; they are then dried over sodium sulphate and afterwards concentrated in vacuo (ca. 12 Torr) to obtain 1'-(3-chloropropionyl)-spiro[bicyclo[2.2.2]octane-2,3'-piperidine].

Workup

  1. additionAn addition
  2. customprecipitates in liquid form
  3. extractionThe mixture is extracted three times with 50 ml of methylene chloride each time
  4. washThe methylene chloride extracts are washed separately in each case once with saturated sodium bicarbonate solution and twice with water
  5. dry with materialthey are then dried over sodium sulphate
  6. concentrationafterwards concentrated in vacuo (ca. 12 Torr)

Sources & evidence

ORD record
ord-615cf59561cd498188e2ccc63016445f
Source dataset
uspto-grants-1977_03
Patent number
US04015007

Reaction notes

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