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

HRID 1742598

Reaction equation

HRID 1742598 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

5

Reactant 4

HCID 7965CyclohexylamineHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 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°.

Workup

  1. customThe crude product was purified by recrystallisation from cyclohexane

Sources & evidence

ORD record
ord-7b62bea8052343679696fa051021d1ca
Source dataset
uspto-grants-1994_08
Patent number
US05340812

Linked notes

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