Morpholine → 4-(Cyanoacetyl)morpholine

HRID 639142Notes

Reaction equation

HRID 639142 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].[NH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.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>[N:7]1([C:4](=[O:6])[CH2:3][C:1]#[N:2])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1

Participants

9

Reactant 4

HCID 8083MorpholineHCID 9740Cyanoacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 2292794-(Cyanoacetyl)morpholine

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, 563 mg (6.47 mmol) morpholine, 794 mg (5.88 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 1.12 g (5.88 mmol) 1-(3-dimethylaminopropyl)-3-ethylcarbodimide 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-2d7ea12858164a89a916edabe4b0cbc4
Source dataset
uspto-grants-2010_04
Patent number
US07691854B2

Reaction notes

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