Triethylamine → N-cyano-N'-(2-hydroxy-1-methyl-2-phenylethyl)-2-pyridinecarboximidamide

HRID 374141

Reaction equation

HRID 374141 reaction equation
[C:1]([N:3]=[C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)OC)#[N:2].[CH3:13][CH:14]([NH2:23])[CH:15]([OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl.C(N(CC)CC)C>CO>[C:1]([NH:3][C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)=[N:23][CH:14]([CH3:13])[CH:15]([OH:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90652-Amino-1-phenylpropan-1-ol hydrochlorideHCID 100121892-Pyridinecarboximidic acid, N-cyano-, methyl ester

Product 1

HCID 19734525N-cyano-N'-(2-hydroxy-1-methyl-2-phenylethyl)-2-pyridinecarboximidamideYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl N-cyano-2-pyridinecarboximidate (0.24 g, 1.5 mmol) was dissolved in methanol (5 ml), DL-phenylpropanolamine hydrochloride (0.31 g. 1.7 mmol, supplied by Tokyo Chemical Industry Co., Ltd.) and triethylamine (0.17 g, 1.7 mmol) were added, and the resulting mixture was stirred at room temperature for 5 solution was concentrated under reduced pressure, and the residue thus obtained was extracted with ethyl acetate (30 ml×3). The ethyl acetate layer was washed with water (100 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrated residue thus obtained was crystallized from diethyl ether to give the title compound (0.23 g, 0.8 mmol, yield: 54%) as colorless crystals.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customthe residue thus obtained
  3. extractionwas extracted with ethyl acetate (30 ml×3)
  4. washThe ethyl acetate layer was washed with water (100 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe concentrated residue thus obtained
  8. customwas crystallized from diethyl ether

Sources & evidence

ORD record
ord-1979016b594c43b7a64075895732b8a8
Source dataset
uspto-grants-1992_11
Patent number
US05166347

Linked notes

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