Triethylamine → tert-Butyl 4-(1H-indol-3-yl)piperazine-1-carboxylate

HRID 641888Notes

Reaction equation

HRID 641888 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)=[CH:5]1)(=O)C.CCN(CC)CC>CO>[C:22]([O:21][C:19]([N:16]1[CH2:17][CH2:18][N:13]([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[NH:4][CH:5]=2)[CH2:14][CH2:15]1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 59259291tert-butyl 4-(1-acetyl-1H-indol-3-yl)piperazine-1-carboxylate

Product 1

HCID 44828736tert-Butyl 4-(1H-indol-3-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a 250 mL round bottom flask was placed a solution of tert-butyl 4-(1-acetyl-1H-indol-3-yl)piperazine-1-carboxylate (2.6 g, 7.58 mmol) in methanol (80 mL). To the mixture was added Et3N (2.3 g, 22.73 mmol). The resulting solution was allowed to react, with stirring, for 1 hour while the temperature was maintained at reflux in a bath of oil. The reaction progress was monitored by LCMS and TLC (ethyl acetate/petroleum ether=1:1). The mixture was concentrated by evaporation under vacuum using a rotary evaporator. The resulting solution was diluted with 200 mL of ethyl acetate. The resulting mixture was washed 3 times with 150 mL of NaCl(aq.). The residue was purified by eluting through a column with a 10:1 petroleum ether/ethyl acetate solvent system. This resulted in 2.1 g (89%) of tert-butyl 4-(1H-indol-3-yl)piperazine-1-carboxylate as a light pink solid.

Workup

  1. customInto a 250 mL round bottom flask was placed
  2. customto react
  3. temperaturewas maintained
  4. temperatureat reflux in a bath of oil
  5. concentrationThe mixture was concentrated by evaporation under vacuum
  6. customa rotary evaporator
  7. additionThe resulting solution was diluted with 200 mL of ethyl acetate
  8. washThe resulting mixture was washed 3 times with 150 mL of NaCl(aq.)
  9. customThe residue was purified
  10. washby eluting through a column with a 10:1 petroleum ether/ethyl acetate solvent system
  11. customThis resulted in 2.1 g (89%) of tert-butyl 4-(1H-indol-3-yl)piperazine-1-carboxylate as a light pink solid

Sources & evidence

ORD record
ord-2f3772854eaf43548cf23157bd0e6ff6
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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