Chloroacetonitrile → 2-(4-Hydroxyiminopiperidin-1-yl)-2-iminoethylchloride hydrochloride

HRID 622413Notes

Reaction equation

HRID 622413 reaction equation
[Cl:1][CH2:2][C:3]#[N:4].[Na].Cl.[OH:7][N:8]=[C:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1>CO>[ClH:1].[OH:7][N:8]=[C:9]1[CH2:14][CH2:13][N:12]([C:3](=[NH:4])[CH2:2][Cl:1])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 5360545SodiumHCID 19106851N-(piperidin-4-ylidene)hydroxylamine hydrochloride

Product 1

HCID 212929432-(4-Hydroxyiminopiperidin-1-yl)-2-iminoethylchloride hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.63 ml of chloroacetonitrile was added to a solution of 23 mg of metallic sodium in 4 ml of absolute methanol, and the mixture was stirred for about 30 minutes at room temperature. 1.5 g of 4-hydroxyiminopiperidine hydrochloride were then added and the stirring was continued for 2 hours, during which time a precipitate separated out. 25 ml of anhydrous ether were added to the reaction mixture, and the precipitated crystals were collected by filtration and washed with ether, giving 2.22 g of 2-(4-hydroxyiminopiperidin-1-yl)-2-iminoethylchloride hydrochloride.

Workup

  1. waitthe stirring was continued for 2 hours, during which time
  2. customa precipitate separated out
  3. addition25 ml of anhydrous ether were added to the reaction mixture
  4. filtrationthe precipitated crystals were collected by filtration
  5. washwashed with ether

Sources & evidence

ORD record
ord-acbee8e0ac844585b6648f235f82bb18
Source dataset
uspto-grants-1988_09
Patent number
US04771046

Reaction notes

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