Chloroform → N-benzyl-3-(5-phenyl-1,2,3-triazol-1-yl)pyrrolidine

HRID 1743003Notes

Reaction equation

HRID 1743003 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.[C:16]1([C:22]#[CH:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(Cl)(Cl)Cl.CCCCCC>C1C=CC=CC=1.CO>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([N:13]2[C:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:23][N:15]=[N:14]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 8058HexaneHCID 10821PhenylacetyleneHCID 114242213-Azido-1-benzylpyrrolidine

Product 1

HCID 19006017N-benzyl-3-(5-phenyl-1,2,3-triazol-1-yl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

A solution of N-benzyl-3-azido pyrrolidine (3 g, 0.0148 mol) and phenyl-acetylene (3 g, 0.0292 mol) in benzene (30 ml) was heated under reflux for 48 hrs. The reaction mixture was concentrated to oil from which the title compounds were isolated by column chromatography using silica gel and a mixture of CHCl3, hexane, MeOH (4:4:1) as eluant. N-benzyl-3-(5-phenyl-1,2,3-triazol-1-yl)pyrrolidine was obtained as oil. Yield: 1 g (22.17%). 1H NMR (CDCl3) δ: 2.32-2.51 (m, 2H), 2.88-3.13 (m, 2H), 3.80 (s, 2H), 5.00 (p, 1H), 7.20-7.53 (m, 10H), 7.67 (s, 1H). N-benzyl-3-(4-phenyl-1,2,3-triazol-1-yl)pyrrolidine, oil, yield 3.0 g. 1H NMR (CDCl3) δ: 2.05-2.22 (m, 1H), 2.30-2.69 (m, 2H), 2.75-3.25 (m, 3H), 5.20- 5.33 (m, 1H), 7.23-7.51 (m, 8H), 7.81-7.92 (m, 2H), 8.06 (s, 1H).

Workup

  1. temperatureunder reflux for 48 hrs
  2. concentrationThe reaction mixture was concentrated to oil from which the title compounds
  3. customwere isolated by column chromatography

Sources & evidence

ORD record
ord-61ba496b467a4a9d8a8f432525c26c6f
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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