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

HRID 1769620

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-80e17721ba31412aa57fade695b834bd
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05382583

Linked notes

Loading…