Stannous Chloride → 2-(Methyloxy)-4-{4-[2-(methylsulfonyl)ethyl]-1-piperidinyl}aniline

HRID 419585Notes

Reaction equation

HRID 419585 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.Cl[Sn]Cl>C1COCC1.Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:13][CH2:14][CH:15]([CH2:18][CH2:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH2:16][CH2:17]2)[CH:6]=[CH:7][C:8]=1[NH2:9]

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 666498721-[3-(Methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperidine

Product 1

HCID 666497682-(Methyloxy)-4-{4-[2-(methylsulfonyl)ethyl]-1-piperidinyl}anilineYield 100%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 1-[3-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperidine (0.42 g, 1.3 mmol) in THF (60 mL) cooled to 0° C. was added SnCl2 (1.0 g, 5.4 mmol) dissolved in conc. HCl dropwise. The solution was stirred overnight at room temperature (TLC confirms consumption of starting material). The mixture was cooled to 0° C. and quenched with 6 N NaOH (25 mL). The solution was poured into EtOAc and H2O was washed with brine, back extracted with EtOAc, dried (MgSO4), filtered, and rotovaped down to give the title compound of step B (0.39 g, 1.3 mmol, 96%). 1H NMR (400 MHz, CDCl3) δ 1.18-1.29 (m, 2H), 1.31-1.43 (m, 1H), 1.57-1.65 (m, 2H), 1.70 (d, J=12.5 Hz, 2H), 2.37-2.43 (m, 2H), 2.92 (s, 3H), 3.07-3.14 (m, 2H), 3.34 (d, J=11.5 Hz, 2H), 3.69 (s, 3H), 4.16 (br. s., 2H), 6.25 (d, J=7.7 Hz, 1H), 6.40-6.48 (m, 2H).

Workup

  1. custom(TLC confirms consumption of starting material)
  2. temperatureThe mixture was cooled to 0° C.
  3. customquenched with 6 N NaOH (25 mL)
  4. additionThe solution was poured into EtOAc and H2O
  5. washwas washed with brine
  6. extractionback extracted with EtOAc
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered

Sources & evidence

ORD record
ord-9f625c9bb37d4147b6002c9b9afa4c5b
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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