Morpholine → Morpholino(1H-pyrazol-4-yl)methanone

HRID 215764Notes

Reaction equation

HRID 215764 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[CH:3]=[N:2]1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>C(Cl)(Cl)Cl>[NH:1]1[CH:5]=[C:4]([C:6]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[O:8])[CH:3]=[N:2]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 3015937Pyrazole-4-carboxylic acid

Product 1

HCID 20784942Morpholino(1H-pyrazol-4-yl)methanoneYield 58.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of 1H-pyrazole-4-carboxylic acid (1.05 g), 1-{3-(dimethylamino)propyl}-3-ethylcarbodiimide hydrochloride (2.5 g), 1-hydroxybenzotriazole hydrate (1.6 g) and morpholine (1.2 g) in chloroform (18 mL) was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: chloroform:methanol=100:0 to 95:5) and silica gel column chromatography (eluting solvent: chloroform:methanol=100:0 to 90:10). The resulting colorless solid was washed with ethyl acetate to give the titled compound (1.00 g) as a colorless solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: chloroform:methanol=100:0 to 95:5) and silica gel column chromatography (eluting solvent: chloroform:methanol=100:0 to 90:10)
  3. washThe resulting colorless solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-5b02a4dafd844a279dd066b9642a8a7d
Source dataset
uspto-grants-2012_06
Patent number
US08193176B2

Reaction notes

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