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

Reaction equation

[Cl:1][CH2:2][C:3]#[N:4].[Na].Cl.[C:7]([O:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)(=[O:9])[NH2:8]>CO>[ClH:1].[C:7]([O:10][CH:11]1[CH2:16][CH2:15][N:14]([C:3](=[NH:4])[CH2:2][Cl:1])[CH2:13][CH2:12]1)(=[O:9])[NH2:8]

Participants

Procedure

5.29 ml of chloroacetonitrile were added to a solution of 192 mg of metallic sodium in 80 ml of anhydrous methanol, and the mixture was stirred at room temperature for one hour. 15.10 g of 4-carbamoyloxypiperidine hydrochloride were than added, and the mixture was stirred for a further 2 hours. The reaction mixture was worked up in the same manner as in Example 1(1), giving 21.00 g of 2-(4-carbamoyloxypiperidin-1-yl)-2-iminoethylchloride hydrochloride.