HCID 22049016, compound → tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate

HRID 1473058Notes

Reaction equation

HRID 1473058 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O>CCO.CN(C=O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]2)=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 22049016HCID 22049016, compound

Product 1

HCID 21940085tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of tert-butyl 4-(4-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate (I43) (0.570 g, 1.87 mmol) in EtOH (5 mL) and DMF (5 mL) was added to a solution of 10% Pd/C (200 mg) in DMF (10 mL). The reaction was stirred at room temperature for 24 hours under an atmosphere of hydrogen. The reaction was filtered through a pad of celite and washed through with EtOAc (130 mL). The solvent was removed in vacuo to yield a brown oil which was purified by column chromatography on silica gel (0-50% EtOAc in petroleum benzine 40-60° C.) to afford the title compound (I44) (0.46 g, 89%) as a crystalline solid; 1H NMR (400 MHz, CDCl3) δ 7.02-6.96 (m, 2H), 6.67-6.61 (m, 2H), 4.21 (bs, 2H), 3.57 (s, 2H), 2.77 (t, J=12.2 Hz, 2H), 2.53 (tt, J12.1, 3.5 Hz, 1H), 1.77 (d, J=13.3 Hz, 2H), 1.64-1.50 (m, peak obscured by solvent), 1.48 (s, 9H). LCMS Method C: rt 4.77 min; m/z 221 [M−tButyl+2H]+, 177 [M-Boc+2H]+.

Workup

  1. filtrationThe reaction was filtered through a pad of celite
  2. washwashed through with EtOAc (130 mL)
  3. customThe solvent was removed in vacuo
  4. customto yield a brown oil which
  5. customwas purified by column chromatography on silica gel (0-50% EtOAc in petroleum benzine 40-60° C.)

Sources & evidence

ORD record
ord-659916436cff43dd99c6b79bfcbc4230
Source dataset
uspto-grants-2015_04
Patent number
US09012461B2

Reaction notes

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