2,2-Diphenylethylamine → HCID 19734493, compound

HRID 327118Notes

Reaction equation

HRID 327118 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:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:22][NH2:23])[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:23][CH2:22][CH:21]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)#[N:2]

Participants

4

Reactant 2

HCID 775752,2-DiphenylethylamineHCID 100812013-Pyridinecarboximidic acid, N-cyano-, 1-methylethyl ester

Product 1

HCID 19734493HCID 19734493, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Isopropyl N-cyano-3-pyridinecarboximidate (0.50 g, 2.6 mmol) was dissolved .in methanol (10 ml), and 2,2- diphenylethylamine (0.58 g, 2.9 mmol) was added. The mixture was stirred at room temperature for 2 hours. 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 to give N-cyano-N'-(2,2-diphenylethyl)-3-pyridinecarboximidamide (0.61 g, 1.9 mmol, yield: 71%) as colorless syrup. Next, to this syrup was added a 5% hydrogen chloride solution in methanol (2.5 ml). The solution was crystallized from methanol-diethyl ether to give N-cyano-N'-(2,2-diphenylethyl)-3-pyridinecarboximidamide hydrochloride as colorless powder.

Workup

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

Sources & evidence

ORD record
ord-bfbb6bb524784063ad8bbc548cb6bbf1
Source dataset
uspto-grants-1993_12
Patent number
US05272164

Reaction notes

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