Cyclohexylamine → N-cyclohexyl-2-phenylprop-2-enamide

HRID 37367

Reaction equation

[C:1]([OH:11])(=O)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:3].CN1CCOCC1.ClC(OCC(C)C)=O.[CH:27]1([NH2:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>>[CH:27]1([NH:33][C:1](=[O:11])[C:2]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH2:3])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

Reactant 4

HCID 7965Cyclohexylamine

HCID 79724-Methylmorpholine

HCID 62365Isobutyl chloroformate

HCID 68114Atropic acid

Product 1

HCID 343735N-cyclohexyl-2-phenylprop-2-enamideYield 28.9%

Procedure

This compound was made from atropic acid (10.48 g, 70.8 mmol), N-methylmorpholine (7.8 ml, 70.9 mmol), iso-butyl chloroformate (9.2 ml, 70.9 mmol), and cyclohexylamine (8.1 ml, 70.7 mmol) using the procedure described in Example 3. The crude product was purified by recrystallisation from cyclohexane to give the product (4.69 g), as white crystals, m.p. 131°-133°. (Found: C, 78.7; H, 8.8; N, 5.95. C15H19NO requires C, 78.6; H, 8.35; N, 6.1%.)

Workup

customThe crude product was purified by recrystallisation from cyclohexane

Sources & evidence

ORD record: ord-5664a6be0a904b4ebe4b4d96ac6e8567
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05420278

Linked notes

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