Hydrochloric Acid → 2-chloro-N-(cyclohexylmethyl)acetamide

HRID 483841Notes

Reaction equation

HRID 483841 reaction equation
[CH:1]1([CH2:7][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:16][CH2:17][C:18](Cl)=[O:19].Cl>C(OCC)C>[CH:1]1([CH2:7][NH:8][C:18](=[O:19])[CH2:17][Cl:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 76688Cyclohexanemethylamine

Product 1

HCID 23899892-chloro-N-(cyclohexylmethyl)acetamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

5.66 Grams of cyclohexylmethylamine is dissolved in 200 ml of diethyl ether. Thereto is added 5.06 g of triethylamine. To the resulting mixture is dropwise added, with ice cooling, a solution of 5.65 g of chloroacetyl chloride dissolved in 150 ml of diethyl ether. The mixture is stirred for 1 hour at room temperature and then acidified with 5% hydrochloric acid. The mixture is extracted with diethyl ether. The extract is washed with water and dried with anhydrous magnesium sulfate. The solvent is removed by evaporation and the residue is recrystallized from n-hexane to obtain 6.7 g of N-cyclohexylmethyl-N-(α-chloroacetyl)amine.

Workup

  1. additionTo the resulting mixture is dropwise added, with ice cooling
  2. extractionThe mixture is extracted with diethyl ether
  3. washThe extract is washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent is removed by evaporation
  6. customthe residue is recrystallized from n-hexane

Sources & evidence

ORD record
ord-cc59061630a24accb7a98a5f05daa463
Source dataset
uspto-grants-1993_07
Patent number
US05227381

Reaction notes

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