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

HRID 2379692

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 C9.2 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-cf2b8c01a3e149428f533c86fdc1e0b3
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05364849

Linked notes

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