Ethyl 1-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]piperidine-4-carboxylate → Ethyl 1-[4-(3-aminophenyl)-1,3-thiazol-2-yl]piperidine-4-carboxylate

HRID 1028147Notes

Reaction equation

HRID 1028147 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[C:12]([N:15]3[CH2:20][CH2:19][CH:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16]3)[S:13][CH:14]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[C:12]([N:15]3[CH2:20][CH2:19][CH:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16]3)[S:13][CH:14]=2)[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 71075037Ethyl 1-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]piperidine-4-carboxylate

Product 1

HCID 77231056Ethyl 1-[4-(3-aminophenyl)-1,3-thiazol-2-yl]piperidine-4-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of the ethyl 1-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]piperidine-4-carboxylate (457 mg, 1.26 mmol) in ethyl acetae (10 mL) and acetic acetic acid (1 mL) was added 10% palladium on carbon (135 mg, 0.126 mmol) and the mixture was placed under an atmosphere of H2 (balloon). The mixture was stirred for 3 hours was then filtered through celite. The filtrate was concentrated under reduced pressure. The resulting residue was purified by CombiFlash (20-60% ethyl acetate:hexanes) provided 250 mg (0.754 mmol, 60% yield) of ethyl 1-[4-(3-aminophenyl)-1,3-thiazol-2-yl]piperidine-4-carboxylate.

Workup

  1. filtrationwas then filtered through celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by CombiFlash (20-60% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-106900a4a2b940e4a01ce58cf73acda3
Source dataset
uspto-grants-2014_05
Patent number
US08735417B2

Reaction notes

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