2-(4-Chlorophenyl)ethylamine → HCID 10039554, compound

HRID 327112Notes

Reaction equation

HRID 327112 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].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][NH2:24])=[CH:18][CH:17]=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][C:19]1[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=1)#[N:2]

Participants

4

Reactant 2

HCID 674302-(4-Chlorophenyl)ethylamineHCID 100812013-Pyridinecarboximidic acid, N-cyano-, 1-methylethyl ester

Product 1

HCID 10039554HCID 10039554, compoundYield 156.3%

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 2-(4-chlorophenyl)ethylamine (0.55 g, 3.5 mmol) was added. The mixture was stirred at room temperature for 2.5 hours. After the reaction was completed, the reaction solution was concentrated under reduced pressure. The residual concentrate 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 the concentrated residue thus obtained was further crystallized from methanol-diethyl ether to give the title compound (0.71 g, 2 5 mmol, yield: 79%) as colorless powder.

Workup

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

Sources & evidence

ORD record
ord-f74678f843fe4e1da114020a99ccc7b2
Source dataset
uspto-grants-1993_12
Patent number
US05272164

Reaction notes

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