Ammonia → Piperazine, 1-(7-benzofuranyl)-

HRID 1952764Notes

Reaction equation

HRID 1952764 reaction equation
FC(F)(F)C(O)=O.[O:8]1[CH:12]=[CH:11][C:10]2[CH:13]=[CH:14][CH:15]=[C:16]([N:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]3)[C:9]1=2.O.N>ClCCl>[O:8]1[CH:12]=[CH:11][C:10]2[CH:13]=[CH:14][CH:15]=[C:16]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:9]1=2

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 6422Trifluoroacetic acidHCID 23300012Tert-butyl 4-(7-benzo[b]furanyl)piperazine-1-carboxylate

Product 1

HCID 10465458Piperazine, 1-(7-benzofuranyl)-Yield 91.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 ml) was added dropwise at 20° C. under nitrogen to a cooled solution of tert-butyl 4-(7-benzo[b]furanyl)piperazine-1-carboxylate (1.66 g) in dichloromethane (5 ml). The solution was stirred at ambient temperature for 1 hour, then poured into cold water (50 ml). The mixture was basified by the addition of aqueous ammonia solution, then the product was extracted into dichloromethane (2×50 ml). The combined organic extracts were washed with brine (100 ml), dried (MgSO4), and the solvent removed in vacuo to give 1-(7-benzo[b]furanyl)piperazine (1.02 g).

Workup

  1. extractionthe product was extracted into dichloromethane (2×50 ml)
  2. washThe combined organic extracts were washed with brine (100 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-1a53f00f6ab24b268f894a684125ceac
Source dataset
uspto-grants-2000_09
Patent number
US06114334

Reaction notes

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