1-(3-Nitropyridin-4-yl)-4-(tetrahydrofuran-3-yl)piperazine → 4-(4-(Tetrahydrofuran-3-yl)piperazin-1-yl)pyridin-3-amine

HRID 524870Notes

Reaction equation

HRID 524870 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][N:13]([CH:16]2[CH2:20][CH2:19][O:18][CH2:17]2)[CH2:12][CH2:11]1)([O-])=O>CO.[Pd]>[O:18]1[CH2:19][CH2:20][CH:16]([N:13]2[CH2:14][CH2:15][N:10]([C:9]3[CH:8]=[CH:7][N:6]=[CH:5][C:4]=3[NH2:1])[CH2:11][CH2:12]2)[CH2:17]1

Participants

4

Reactant 1

HCID 867209281-(3-Nitropyridin-4-yl)-4-(tetrahydrofuran-3-yl)piperazine

Product 1

HCID 867209294-(4-(Tetrahydrofuran-3-yl)piperazin-1-yl)pyridin-3-amineYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23938PalladiumSolvent

Procedure

A solution of 1-(3-nitropyridin-4-yl)-4-(tetrahydrofuran-3-yl)piperazine (316 mg, 1.13 mmol) in MeOH (15 mL), Pd on C (10%, wet, Degussa) (120 mg) was stirred overnight at RT under an hydrogen atmosphere (balloon). The mixture was filtered through a Celite pad and concentrated under reduced pressure. The crude was redissolved in MeOH and loaded into a MeOH pre-washed SCX column, rinsed with MeOH and the product was released with methanolic ammonia. The ammonia extracts were concentrated under reduced pressure to give 4-(4-(tetrahydrofuran-3-yl)piperazin-1-yl)pyridin-3-amine as a solid which was used in next step without further purification. (300 mg, purity 77%, yield 82%). MS (ES+) 249.2.

Workup

  1. filtrationThe mixture was filtered through a Celite pad
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe crude was redissolved in MeOH
  4. washrinsed with MeOH
  5. concentrationThe ammonia extracts were concentrated under reduced pressure

Sources & evidence

ORD record
ord-89fc0e59ec3b4d1b946a482078c0f25a
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

Loading…