3,3-Diphenylpropylamine → N-cyano-N'-(3,3-diphenylpropyl)-3-pyridinecarboximidamide

HRID 374169Notes

Reaction equation

HRID 374169 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([CH:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[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][CH:21]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)#[N:2]

Participants

4

Reactant 2

HCID 796983,3-DiphenylpropylamineHCID 100812013-Pyridinecarboximidic acid, N-cyano-, 1-methylethyl ester

Product 1

HCID 19734577N-cyano-N'-(3,3-diphenylpropyl)-3-pyridinecarboximidamideYield 63%

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 3,3-diphenylpropylamine (0.74 g, 3.5 mmol) was added. The mixture was stirred at room temperature for 1 hour. 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, 50 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 (0.68 g, 2.0 mmol, yield: 63%) as colorless powder.

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-dcc478d7345e4b47b30d9c25ac4b9a28
Source dataset
uspto-grants-1992_11
Patent number
US05166347

Reaction notes

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