Propylamine → 2-cyano-N-propylacetamide

HRID 639144Notes

Reaction equation

HRID 639144 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].[CH2:7]([NH2:10])[CH2:8][CH3:9].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.CN(C)C1C=CN=CC=1.C(OCC)(=O)C.O>[C:1]([CH2:3][C:4]([NH:10][CH2:7][CH2:8][CH3:9])=[O:6])#[N:2]

Participants

9

Reactant 4

HCID 7852PropylamineHCID 9740Cyanoacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 44299652-cyano-N-propylacetamide

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

500 mg (5.88 mmol) Cyanoacetic acid are dissolved in 30 ml dimethylformamide, 382 mg (6.47 mmol) n-propylamine, 874 mg (6.47 mmol) 1-hydroxy-1H-benzotriazole hydrate and 718 mg (5.88 mmol) 4-dimethylaminopyridine are added. The reaction mixture is stirred at 0° C., then 1.24 g (6.47 mmol) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride are added. The reaction mixture is stirred at room temperature for 18 hours, then water and ethyl acetate are added. The organic phase is dried over sodium sulfate and evaporated to dryness in vacuo. The residue is purified by preparative HPLC.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 18 hours
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customevaporated to dryness in vacuo
  4. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-a8b1980d808b4158916c639769a771ae
Source dataset
uspto-grants-2010_04
Patent number
US07691854B2

Reaction notes

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