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

HRID 1736647Notes

Reaction equation

HRID 1736647 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-c6ee4328a78b4152bb6aebc83b354bc5
Source dataset
uspto-grants-1996_07
Patent number
US05541326

Reaction notes

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