N-(2-Aminoethyl)piperidine → HCID 58424866, compound

HRID 2409413Notes

Reaction equation

HRID 2409413 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[C:17]3[CH:18]=[CH:19][C:20]([C:22](O)=[O:23])=[CH:21][C:16]=3[C:15]3[N:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:9]2=[O:25])=[CH:5][CH:4]=1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[NH2:51][CH2:52][CH2:53][N:54]1[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]1>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[C:17]3[CH:18]=[CH:19][C:20]([C:22]([NH:51][CH2:52][CH2:53][N:54]4[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]4)=[O:23])=[CH:21][C:16]=3[C:15]3[N:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:9]2=[O:25])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 33944N-(2-Aminoethyl)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 58424937HCID 58424937, compound

Product 1

HCID 58424866HCID 58424866, compoundYield 193.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (30 mg, 0.09 mmol) prepared in Step 1, 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (EDC, 48 mg, 0.25 mmol), and 1-hydroxy-benzotriazole hydrate (HOBt, 34 mg, 0.25 mmol) were dissolved in N,N-dimethylformamide (5 ml) and added with 1-(2-aminoethyl)piperidine (0.033 ml, 0.23 mmol) at room temperature. The resulting mixture was stirred for 18 hours and poured into ice water. After extraction with chloroform, the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was then purified by flash column chromatography (chloroform:methanol=7:1) to obtain the title compound (82 mg, yield: 92%, white solid).

Workup

  1. extractionAfter extraction with chloroform
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was then purified by flash column chromatography (chloroform:methanol=7:1)

Sources & evidence

ORD record
ord-1c8e7a91206e4fd1b23d285062530e5f
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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