HCID 66710890, compound → (2S)-1-[4-(4-Aminophenyl)piperazin-1-yl]propan-2-ol

HRID 1261947Notes

Reaction equation

HRID 1261947 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C@@H:17]([OH:19])[CH3:18])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:11][CH2:12][N:13]([CH2:16][C@@H:17]([OH:19])[CH3:18])[CH2:14][CH2:15]2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 66710890HCID 66710890, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 28408104(2S)-1-[4-(4-Aminophenyl)piperazin-1-yl]propan-2-olYield 88.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-1-[4-(4-Nitro-phenyl)-piperazin-1-yl]-propan-2-ol (1.60 g, 0.00603 mol) was dissolved in Methanol (35.0 mL) and the solution was carefully added to a Parr vessel containing 10% Palladium on Carbon (90.10, carbon black. Palladium, 0.500 g, 0.0375 mol) under nitrogen. The reaction was then placed on a Parr hydrogenator and was allowed to shake until uptake of hydrogen had ceased (overnight). Catalyst was removed via filtration and filtrate was reduced en vacuo to afford 1.25 g of (5)-1-[4-(4-Amino-phenyl)-piperazin-1-yl]-propan-2-ol as a white powder. (M+H)=236.21. 1H NMR (400 MHz, DMSO, d6) δ 6.66 (d, 2H, J=8.72 Hz), 6.48 (d, 2H, J=8.72 Hz), 4.53 (s, 2H), 4.26 (d, 1H, J=4.00 Hz), 3.77 (m, 1H), 2.88 (m, 4H), 2.54 (m, 4H), 2.26 (m, 1H), 2.18 (m, 1H), 1.04 (d, 3H, J=6.17 Hz).

Workup

  1. additionthe solution was carefully added to a Parr vessel
  2. custom(overnight)
  3. customCatalyst was removed via filtration and filtrate

Sources & evidence

ORD record
ord-c480229fd70f4b2dba734eef436f0508
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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