(R)-2-((1-butyrylpiperidin-2-yl)methoxy)-6-nitrobenzonitrile → (R)-2-amino-6-((1-butyrylpiperidin-2-yl)methoxy)benzonitrile

HRID 332967Notes

Reaction equation

HRID 332967 reaction equation
[C:1]([N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C@@H:7]1[CH2:12][O:13][C:14]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[C:15]=1[C:16]#[N:17])(=[O:5])[CH2:2][CH2:3][CH3:4].[H][H]>C(O)C.[Pd]>[NH2:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:14]([O:13][CH2:12][C@H:7]2[CH2:8][CH2:9][CH2:10][CH2:11][N:6]2[C:1](=[O:5])[CH2:2][CH2:3][CH3:4])[C:15]=1[C:16]#[N:17]

Participants

5

Reactant 2

HCID 86714289(R)-2-((1-butyrylpiperidin-2-yl)methoxy)-6-nitrobenzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 86714288(R)-2-amino-6-((1-butyrylpiperidin-2-yl)methoxy)benzonitrileYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (R)-2-((1-butyrylpiperidin-2-yl)methoxy)-6-nitrobenzonitrile (Example 16b, 1.5 g, 4.53 mmol) in ethanol (40 mL) was added 10% Pd/C (300 mg). The reaction mixture was charged with hydrogen balloon at room temperature overnight then filtered through celite and concentrated under reduced pressure. The residue was purified by Biotage SP-1 (40s column) eluting with EtOAc/Hexane (10%-70%) to give the desired product as an oil (1.1 g, 81%). 1H NMR (400 MHz, DMSO-d6) δ 0.86 (t, J=7.2 Hz, 3H), 1.46-1.65 (m, 7H), 1.77-1.85 (m, 1H), 2.24-2.30 (m, 1H), 2.38-2.42 (m, 1H), 2.56-2.63 (m, 0.5H), 3.1-3.16 (m, 0.5H), 3.71-3.74 (m, 0.3H), 3.92-3.98 (m, 1H), y 2H), 7.15-7.19 (m, 1H). MS 302 (MH+).

Workup

  1. filtrationthen filtered through celite and
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by Biotage SP-1 (40s column)
  4. washeluting with EtOAc/Hexane (10%-70%)

Sources & evidence

ORD record
ord-4df8c1e7df6946a58bf751354704868a
Source dataset
uspto-grants-2014_11
Patent number
US08877922B2

Reaction notes

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