Hydrochloric Acid → 4-(3-Aminophenyl)piperidine

HRID 2087143Notes

Reaction equation

HRID 2087143 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1>O1CCOCC1.ClCCl>[NH:12]1[CH2:13][CH2:14][CH:9]([C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=2)[NH2:2])[CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22049268tert-Butyl 4-(3-aminophenyl)piperidine-1-carboxylate

Product 1

HCID 220479094-(3-Aminophenyl)piperidineYield 64.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4 M HCl in dioxane (25 mL) was added to tert-butyl 4-[3-(amino)phenyl]-1-piperidinecarboxylate (2.60 g, 9.00 mmol) in dichloromethane (250 mL). The reaction mixture was stirred at room temperature overnight, concentrated in vacuo, and the residue was dissolved in water (50 mL). The mixture was nuetralized using KOH pellets and extracted with methylene chloride (3×50 mL). The combined organic extracts were dried (MgSO4), concentrated and chromatographed to give the desired product (1.03 g). 1H NMR (400 MHz, CDCl3) δ 7.01 (t, 1H, J=7.6 Hz), 6.62-6.54 (m, 3H), 3.16 (br d, 2H, J=10.3 Hz), 2.75 (dt, 2H, J=2.7, 12.3 Hz), 2.56 (tt, 1H, J=3.6, 12.3 Hz), 1.81 (br d, 2H, J=12.3 Hz), 1.65 (dq, 2H, J=4.0, 12.3 Hz); ESMS m/e: 177.2 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionthe residue was dissolved in water (50 mL)
  3. extractionextracted with methylene chloride (3×50 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. customchromatographed

Sources & evidence

ORD record
ord-f9c41ca0d1634c96bece4e348a2336ae
Source dataset
uspto-grants-2004_04
Patent number
US06727264B1

Reaction notes

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