Ethanol → 2-(4-Benzylpiperazin-1-yl)aniline

HRID 1242718Notes

Reaction equation

HRID 1242718 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH2:11]1)([O-])=O.CCO.O.O.Cl[Sn]Cl.[OH-].[Na+]>C(Cl)Cl>[CH2:16]([N:13]1[CH2:12][CH2:11][N:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH2:1])[CH2:15][CH2:14]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 5181711-Benzyl-4-(2-nitrophenyl)piperazine

Product 1

HCID 45188322-(4-Benzylpiperazin-1-yl)anilineYield 79.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a round-bottomed flask equipped with magnetic stirring was added 1-(2-nitrophenyl)-4-benzylpiperazine (42 g, 160 mmol), EtOH (300 mL), and SnCl2.2H2O (Aldrich) (141 g, 624 mmol), and the reaction mixture was warmed to 60° C. for 5 h. The reaction mixture was treated with 1N NaOH (30 mL) and CH2Cl2. The organic layer was separated, and the aqueous layer was extracted with CH2Cl2 (2×30 mL). All organic fractions were combined, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to afford the amine as a light yellow oil (34 g). MS (ESI, pos. Ion) m/z: 268 (M+H); MS (ESI, neg. Ion) m/z: 266 (M−H). Calc'd for C17H21N3: 267.17.

Workup

  1. customTo a round-bottomed flask equipped
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (2×30 mL)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d3edad8dfae543bfa059e261e55083ab
Source dataset
uspto-grants-2006_10
Patent number
US07115607B2

Reaction notes

Loading…