N-(2-Aminoethyl)piperidine → HCID 131724923, compound

HRID 1349869Notes

Reaction equation

HRID 1349869 reaction equation
[CH:1]1[CH:2]=CC2N(O)N=NC=2[CH:6]=1.C([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1)[N:17]=[C:16]2[C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31]([OH:33])=O)#N.CCN=C=[N:41][CH2:42][CH2:43][CH2:44][N:45]([CH3:47])C.Cl.[NH2:49][CH2:50]CN1CCCCC1>C1COCC1.CN(C=O)C>[C:50]([CH:25]1[CH2:24][O:23][CH:22]([N:18]2[C:19]3[C:15](=[CH:14][CH:13]=[CH:21][CH:20]=3)[C:16]([C:28]3[CH:29]=[C:30]([C:31]([NH:41][CH2:42][CH2:43][CH:44]4[CH2:2][CH2:1][CH2:6][CH2:47][NH:45]4)=[O:33])[CH:34]=[CH:35][CH:36]=3)=[N:17]2)[CH2:27][CH2:26]1)#[N:49]

Participants

7

Reactant 4

HCID 33944N-(2-Aminoethyl)piperidineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22480305HCID 22480305, compound

Product 1

HCID 131724923HCID 131724923, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

HOBT (1.74 g, 12.93 mmol) was added in one portion to a solution of 3-(5-cyano-1-perhydro-2H-pyran-2-yl-1H-indazol-3-yl)benzoic acid (1.50 g, 4.31 mmol) in anhydrous THF (50.0 mL) and anhydrous DMF (20.0 mL) at ambient temperature. After 30 min EDAC.HCl (2.47 g, 12.93 mmol) and 1-(2-aminoethyl)piperidine (1.84 mL, 12.93 mmol) was added and the resultant mixture was stirred for 20 h. The reaction mixture was partitioned between ethyl acetate and water, washed with brine, dried over Na2SO4 and concentrated in vacuo during which the product began to precipitate as a colorless solid. Hexanes were added and the desired product was collected by vacuum filtration (1.8 g, 91% yield) ES-MS (m/z) 458 [M+H]+.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo during which the product
  5. customto precipitate as a colorless solid
  6. additionHexanes were added
  7. filtrationthe desired product was collected by vacuum filtration (1.8 g, 91% yield) ES-MS (m/z) 458 [M+H]+

Sources & evidence

ORD record
ord-33591f0accf842e8b54f87da9cfd1006
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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