Acetylene → N-Benzyl-3-(1,2,3-triazol-1-yl)-pyrrolidine

HRID 1742987Notes

Reaction equation

HRID 1742987 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([N:13]=[N+:14]=[N-:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:16]#[CH:17]>CC(C)=O.C(=O)=O.CC(C)=O>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([N:13]2[CH:17]=[CH:16][N:15]=[N:14]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6326Acetylene2×HCID 114242213-Azido-1-benzylpyrrolidine

Product 1

HCID 19691549N-Benzyl-3-(1,2,3-triazol-1-yl)-pyrrolidine

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 18522661Acetone cardiceSolvent2×

Procedure

A solution of N-benzyl-3-azido-pyrrolidine (1.5 g, 0.0074 mol) in acetone was taken in a steel bomb and cooled in dry ice/acetone bath. To this cold solution acetylene (2.5 mg, 0.096 mol) was added under N2 atmosphere. The sealed steel bomb was then heated in an oil bath at 75° C. for 20 h. The vessel was cooled again in dry ice/acetone bath and excess of acetylene released slowly, while the temperature rose to the room temperature (r.t.). The reaction mixture was concentrated to yellow-brown oil. Crude yield: 2.02 g. Crude compound was purified on silica gel column to obtain the title compound as a light yellow-brown oil. Yield: 1.02 g (60%). 1H NMR (CDCl3) δ: 2.0-3.3 (m, 6H), 3.7 (S, 2H), 5.3 (m, 1H), 7.45 (s, 5H), 7.8 (s, 1H), 7.95 (s, 1H).

Workup

  1. customrose to the room temperature (r.t.)
  2. concentrationThe reaction mixture was concentrated to yellow-brown oil
  3. customCrude compound was purified on silica gel column

Sources & evidence

ORD record
ord-4ff26fa735204ca18f4830c97153b5f7
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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