2-(2-Chlorophenyl)ethylamine → HCID 9817299, compound

HRID 327111Notes

Reaction equation

HRID 327111 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][CH:19]=[CH:18][C:17]=1[CH2:22][CH2:23][NH2:24]>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:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[Cl:15])#[N:2]

Participants

4

Reactant 2

HCID 831172-(2-Chlorophenyl)ethylamineHCID 100812013-Pyridinecarboximidic acid, N-cyano-, 1-methylethyl ester

Product 1

HCID 9817299HCID 9817299, compoundYield 76.9%

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-chlorophenyl)ethylamine (0.45 g, 2.9 mmol) was added. The mixture was stirred at room temperature for 7 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, 30 g) eluting with chloroform-methanol (100:1). The eluted fraction were concentrated under reduced pressure, and the concentrated residue thus obtained was crystallized from methanolhexane to give the title compound (0.56 g, 2.0 mmol, yield: 75%) as colorless crystals.

Workup

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

Sources & evidence

ORD record
ord-cb2e6c01bd104fabb09b5fd769646838
Source dataset
uspto-grants-1993_12
Patent number
US05272164

Reaction notes

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