Propylamine → HCID 67394383, compound

HRID 2400225Notes

Reaction equation

HRID 2400225 reaction equation
[CH:1]1([C:7]([OH:9])=O)[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.[NH2:10][CH2:11][CH2:12][CH3:13].CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>C(Cl)Cl.CC(C)=O.C(Cl)Cl>[CH2:11]([NH:10][C:7]([CH:1]1[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1)=[O:9])[CH2:12][CH3:13]

Participants

7

Reactant 4

HCID 7852PropylamineHCID 209033-Cyclohexene-1-carboxylic acidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 67394383HCID 67394383, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21584124Propan-2-one--dichloromethane (1/1)Solvent

Procedure

Cyclohex-3-enecarboxylic acid (0.71 mmol, 90 mg), NH2CH2CH2CH3 (0.86 mmol, 70 μL) and EDC.HCl (0.86 mmol, 164 mg) were dissolved in CH2Cl2 (3 mL). DIEA (1.43 mmol, 252 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-propylcyclohex-3-enecarboxamide 26 as a white powder (65 mg, 55%). 1H NMR (400 MHz, CDCl3) δ 5.64 (m, 3H), 3.17 (dd, J=8 Hz, J=8 Hz, 2H), 2.30-1.93 (m, 5H), 1.87-1.81 (m, 1H), 1.72-1.59 (m, 1H), 1.43 (m, 2H), 0.87 (t, J=8 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 175.93, 126.94, 125.61, 41.52, 41.22, 28.35, 25.97, 24.80, 23.07, 11.49.

Sources & evidence

ORD record
ord-cf01a84f39114013a3308b070f964ff0
Source dataset
uspto-grants-2014_08
Patent number
US08795647B2

Reaction notes

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