Acetic Acid → HCID 19814218, compound

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([O:16][C:17](=[O:19])N)([C:14]#[CH:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.C(O)(=[O:23])C>>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([O:16][C:17](=[O:19])[O:23][C:14]2=[CH2:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 176Acetic Acid

HCID 260Hydrogen Bromide

HCID 198143061-Benzyl-4-carbamoyloxy-4-ethynylpiperidine

Product 1

HCID 19814218HCID 19814218, compoundYield 59.3%

Procedure

5.16 g of 1-benzyl-4-carbamoyloxy-4-ethynylpiperidine are stirred in 30 ml of 30% by weight solution of hydrogen bromide in acetic acid at room temperature for 6 hours. After evaporating the solvent under reduced pressure and adding 50 ml of water to the residue the base is liberated by sodium hydrogen carbonate. The solid product obtained is filtered, washed to bromide-free with water, dried and recrystallized from n-hexane to give the title compound in 59.3% yield the physical characteristics of which are in agreement with those given in Example 1.