1-{3-[3-(Methyloxy)-4-nitrophenyl]-2-propyn-1-yl}piperidine → 2-(Methyloxy)-4-[3-(1-piperidinyl)propyl]aniline

HRID 419481Notes

Reaction equation

HRID 419481 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]#[C:13][CH2:14][N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>CCOC(C)=O.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:6]=[CH:7][C:8]=1[NH2:9]

Participants

3

Reactant 1

HCID 594528121-{3-[3-(Methyloxy)-4-nitrophenyl]-2-propyn-1-yl}piperidine

Product 1

HCID 594528182-(Methyloxy)-4-[3-(1-piperidinyl)propyl]anilineYield 60%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

1-{3-[3-(methyloxy)-4-nitrophenyl]-2-propyn-1-yl}piperidine (0.29 g, 1.06 mmol) was placed in a 40 mL high vial and dissolved in 10 mL of 1 to 1 EtOAc/MeOH. 5 wt % Platinum(sulfided)/carbon (0.284 g, 0.07 mmol) was added followed quickly by a screw cap septum. The vial was evacuated and filled with N2 six times to remove any oxygen. The vial was then pressurized with H2 (balloon). The solution stirred overnight. The next morning the vessel was evacuated and filled with N2 six times to remove any H2. The solution was filtered through celite and evaporated to afford the title compound of step D (0.156 g, 0.63 mmol, 60%). 1H NMR (400 MHz, CDCl3) δ ppm 6.56-6.64 (m, 3H), 3.83 (s, 3H), 3.40-3.75 (m, 2H), 2.50 (dt, J=19.14, 7.55 Hz, 4H), 2.37-2.45 (m, 2H), 1.86 (dt, J=15.29, 7.74 Hz, 1H), 1.63-1.70 (m, 2H), 1.59 (ddd, J=14.97, 7.55, 1.10 Hz, 2H), 1.45 (s, 1H), 0.92 (td, J=7.33, 1.10 Hz, 2H).

Workup

  1. customcap septum
  2. customThe vial was evacuated
  3. additionfilled with N2 six times
  4. customto remove any oxygen
  5. customThe next morning the vessel was evacuated
  6. additionfilled with N2 six times
  7. customto remove any H2
  8. filtrationThe solution was filtered through celite
  9. customevaporated

Sources & evidence

ORD record
ord-ee32713d85b64674be898724304b35a8
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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