Morpholine → N-(prop-2-yn-1-yl)morpholine-4-carboxamide

HRID 1785112Notes

Reaction equation

HRID 1785112 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:7]([NH:10][C:11](=O)[O:12]C1C=CC([N+]([O-])=O)=CC=1)[C:8]#[CH:9]>ClCCl>[CH2:7]([NH:10][C:11]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[O:12])[C:8]#[CH:9]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 230891794-Nitrophenyl prop-2-ynylcarbamate

Product 1

HCID 45088989N-(prop-2-yn-1-yl)morpholine-4-carboxamideYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Morpholine (510 mg, 5.86 mmol) and 4-nitrophenyl prop-2-yn-1-ylcarbamate (800 mg (80% purity), 2.91 mmol) in dichloromethane (10 ml) were stirred at room temperature for 4 hours and then the reaction solution was purified directly by chromatography on silica using ethyl acetate as eluent to give N-prop-2-yn-1-ylmorpholine-4-carboxamide (453 mg, 92%) as a pale yellow solid; NMR Spectrum: (CDCl3) 2.24 (t, 1H), 3.37 (m, 4H), 3.69 (m, 4H), 4.05 (m, 2H), 4.65 (s, 1H).

Workup

  1. customthe reaction solution was purified directly by chromatography on silica

Sources & evidence

ORD record
ord-899fcc4891e9410c93e903e7568e6b17
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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