Butyric Acid → (S)-2-((1-butyrylpiperidin-3-yl)methoxy)-6-nitrobenzonitrile

HRID 1483931Notes

Reaction equation

HRID 1483931 reaction equation
Cl.[N+:2]([C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][C@H:15]2[CH2:20][CH2:19][CH2:18][NH:17][CH2:16]2)[C:6]=1[C:7]#[N:8])([O-:4])=[O:3].C(N(CC)CC)C.[C:28](O)(=[O:32])[CH2:29][CH2:30][CH3:31].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.CN(C=O)C>[C:28]([N:17]1[CH2:18][CH2:19][CH2:20][C@H:15]([CH2:14][O:13][C:9]2[CH:10]=[CH:11][CH:12]=[C:5]([N+:2]([O-:4])=[O:3])[C:6]=2[C:7]#[N:8])[CH2:16]1)(=[O:32])[CH2:29][CH2:30][CH3:31]

Participants

8

Reactant 5

HCID 264Butyric AcidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 86714270(S)-2-nitro-6-(piperidin-3-ylmethoxy)benzonitrile hydrochloride

Product 1

HCID 86714269(S)-2-((1-butyrylpiperidin-3-yl)methoxy)-6-nitrobenzonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of (S)-2-nitro-6-(piperidin-3-ylmethoxy)benzonitrile hydrochloride (Example 1d, 9.8 g, 32.92 mmol) in CH2Cl2 (550 mL) and DMF (50 mL) was added triethylamine (9.2 mL, 65.84 mmol). After being stirred at room temperature for 5 min., a solution of butyric acid (3.33 mL, 36.21 mmol), EDCI (6.94 g, 36.21 mmol) and HOBt (4.89 g, 36.21 mmol) in DCM (50 mL) was added, and the reaction mixture was then stirred at room temperature overnight. The resulting mixture was diluted with CH2Cl2, washed with 0.5 N HCl, water, NaHCO3 and brine, dried over MgSO4, filtered and evaporated to give the crude product as a light brown gel, used as this in the next step. MS 332 (MH+).

Workup

  1. stirringthe reaction mixture was then stirred at room temperature overnight
  2. washwashed with 0.5 N HCl, water, NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-5544bb0028a7437eb6994ef665705af4
Source dataset
uspto-grants-2016_08
Patent number
US09420814B2

Reaction notes

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