1-[3-(Ethyloxy)-4-nitrophenyl]-4-[1-(2-fluoroethyl)-4-piperidinyl]piperazine → (2-(Ethyloxy)-4-{4-[1-(2-fluoroethyl)-4-piperidinyl]-1-piperazinyl}phenyl)amine

HRID 419399Notes

Reaction equation

HRID 419399 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:13]2[CH2:18][CH2:17][N:16]([CH:19]3[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][F:27])[CH2:21][CH2:20]3)[CH2:15][CH2:14]2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)[CH3:2]>CO.CCOC(C)=O.[Pt]>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:13]2[CH2:18][CH2:17][N:16]([CH:19]3[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][F:27])[CH2:21][CH2:20]3)[CH2:15][CH2:14]2)[CH:7]=[CH:8][C:9]=1[NH2:10])[CH3:2]

Participants

4

Reactant 1

HCID 594526551-[3-(Ethyloxy)-4-nitrophenyl]-4-[1-(2-fluoroethyl)-4-piperidinyl]piperazine

Product 1

HCID 59452599(2-(Ethyloxy)-4-{4-[1-(2-fluoroethyl)-4-piperidinyl]-1-piperazinyl}phenyl)amineYield 74%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of 1-[3-(ethyloxy)-4-nitrophenyl]-4-[1-(2-fluoroethyl)-4-piperidinyl]piperazine (200 mg, 0.53 mmol) and platinum (sulfided, 5 wt. % on carbon, 50 mg, 0.013 mmol) in 20% MeOH/EtOAc (20 mL) was added to a high-pressure hydrogenation reaction flask. The reaction was purged with N2 and vacuum (3×). The reaction was purged with H2 and vacuum (3×). The reaction was then treated with H2 at 50 psi and stirred for approximately 16 h. The reaction was degassed, then poured through a Teflon filter, washing the solid with MeOH and DCM. The filtrate was concentrated under vacuum to give the title compound of step C (136 mg, 0.38 mmol, 74%) as a brown solid. MS (ESI): 351 [M+H]+.

Workup

  1. additionwas added to a high-pressure hydrogenation reaction flask
  2. customThe reaction was purged with N2 and vacuum (3×)
  3. customThe reaction was purged with H2 and vacuum (3×)
  4. additionThe reaction was then treated with H2 at 50 psi
  5. customThe reaction was degassed
  6. additionpoured through a Teflon
  7. filtrationfilter
  8. washwashing the solid with MeOH and DCM
  9. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-a2cba10b4475427aa84373371b861288
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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