3-Cyclohexene-1-carboxylic acid → HCID 67395428, compound

HRID 2400226Notes

Reaction equation

HRID 2400226 reaction equation
[CH:1]1([C:7]([OH:9])=O)[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.CCN=C=N[CH2:15][CH2:16][CH2:17][N:18](C)C.Cl.CCN([CH:28]([CH3:30])[CH3:29])C(C)C.[CH3:31][C:32](C)=O.C(Cl)Cl>C(Cl)Cl>[CH2:17]([NH:18][C:7]([CH:1]1[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1)=[O:9])[CH2:16][CH2:15][CH2:31][CH2:32][CH2:30][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 209033-Cyclohexene-1-carboxylic acidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21584124Propan-2-one--dichloromethane (1/1)

Product 1

HCID 67395428HCID 67395428, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyclohex-3-enecarboxylic acid (1.11 mmol, 140 mg), NH2-octyl (1.33 mmol, 220 μL) and EDC.HCl (1.33 mmol, 255 mg) were dissolved in CH2Cl2 (3 mL). DIEA (2.22 mmol, 393 μL) was added at 0° C., and the reaction was stirred for 16 h at rt. The usual workup and chromatography (Acetone/CH2Cl2/10:90) yielded N-octylcyclohex-3-enecarboxamide 27 as a white powder (215 mg, 82%). 1H NMR (400 MHz, CDCl3) δ 5.77 (s, 1H), 5.63 (s, 2H), 3.18 (dd, J=8 Hz, J=8 Hz, 2H), 2.33-2.00 (m, 5H), 1.86-1.82 (s, 1H), 1.70-1.60 (m, 1H), 1.43 (m, 2H), 1.22 (m, 10H), 0.82 (t, J=8 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 175.89, 126.88, 125.59, 41.46, 39.56, 31.91, 29.81, 29.39, 29.33, 28.32, 27.05, 25.93, 24.79, 22.75, 14.19.

Sources & evidence

ORD record
ord-b9adcf6f3adb428a90227e6988aca6e2
Source dataset
uspto-grants-2014_08
Patent number
US08795647B2

Reaction notes

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