3-Phenylpropylamine → HCID 11777594, compound

HRID 374165Notes

Reaction equation

HRID 374165 reaction equation
[C:1]([N:3]=[C:4]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)OC(C)C)#[N:2].[C:15]1([CH2:21][CH2:22][CH2:23][NH2:24])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CO>[C:1]([NH:3][C:4]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)=[N:24][CH2:23][CH2:22][CH2:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)#[N:2]

Participants

4

Reactant 2

HCID 162593-PhenylpropylamineHCID 100812013-Pyridinecarboximidic acid, N-cyano-, 1-methylethyl ester

Product 1

HCID 11777594HCID 11777594, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Isopropyl N-cyano-3-pyridinecarboximidate (0.60 g, 3.2 mmol) was dissolved in methanol (10 ml), and 3-phenylpropylamine (0.47 g, 3.5 mmol) was added. The mixture was stirred at room temperature for 50 minutes. After the reaction was completed, the reaction solution was concentrated under reduced pressure. The residual concentrate thus obtained was subjected to chromatography on a silica gel column (WAKO GEL C-200, 30 g) eluting with chloroform-methanol (100:1). The eluted fractions were concentrated under reduced pressure and crystallized from methanol-diethyl ether to give the title compound (0.67 g, 2.5 mmol, yield: 80%) as colorless needles.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. concentrationThe residual concentrate thus
  3. customobtained
  4. washeluting with chloroform-methanol (100:1)
  5. concentrationThe eluted fractions were concentrated under reduced pressure
  6. customcrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-3d148132f7834d9db061c1e77f86d346
Source dataset
uspto-grants-1992_11
Patent number
US05166347

Reaction notes

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