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

HRID 1609496Notes

Reaction equation

HRID 1609496 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-70e0c99346764eb5b830a81f6b81d26d
Source dataset
uspto-grants-1995_03
Patent number
US05401740

Reaction notes

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