Trifluoroacetic acid → 4-(1-Phenyl-1,2,3-triazol-4-yl)-1,2,3,6-tetrahydropyridine

HRID 727091Notes

Reaction equation

HRID 727091 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[N:15]=[N:16][N:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:19]1([N:17]2[CH:18]=[C:14]([C:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=3)[N:15]=[N:16]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 197052921-Tert-butoxycarbonyl-4-(1-phenyl-1,2,3-triazol-4-yl)-1,2,3,6-tetrahydropyridine

Product 1

HCID 197052864-(1-Phenyl-1,2,3-triazol-4-yl)-1,2,3,6-tetrahydropyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-tert-butoxycarbonyl-4-(1-phenyl-1,2,3-triazol-4-yl)-1,2,3,6-tetrahydropyridine (816 mg, 2.5 mmol) in dichloromethane (10 ml) was added trifluoroacetic acid (10 ml) and the reaction stirred at room temperature for 35 minutes. The solvent was evaporated in vacuo and the residue basfied by addition of aqueous sodium hydroxide (1M, 30 ml). Water (30 ml) was added and the mixture extracted with dichloromethane (3×30 ml). The combined organic layers were washed with saturated brine (20 ml), dried (K2CO3) and evaporated in vacuo to yield the title compound as a buff solid (486 mg, 86%). δH (CDCl3) 2.59-2.53 (2H, br s, tetrahydropyridinyl CH2), 3.14 (2H, t, J 5.7 Hz, tetrahydropyridinyl CH2), 3.56-3.58 (2H, br s, tetrahydropyridinyl CH2), 6.60 (1H, br s, tetrahydropyridinyl 5-H), 7.40-7.45 (1H, m, ArH), 7.50-7.54 (2H, m, ArH), 7.72-7.75 (2H, m, ArH), 7.84 (1H, s, triazolyl 5-H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionthe residue basfied by addition of aqueous sodium hydroxide (1M, 30 ml)
  3. additionWater (30 ml) was added
  4. extractionthe mixture extracted with dichloromethane (3×30 ml)
  5. washThe combined organic layers were washed with saturated brine (20 ml)
  6. dry with materialdried (K2CO3)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-8331943d7af84e22a45fbfffa726c47d
Source dataset
uspto-grants-1998_01
Patent number
US05712285

Reaction notes

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