Diethyl Ether → N-(6,6-dimethylbicyclo[3.1.1]hept-2-yl)-2-propenamide

Reaction equation

[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].C([N:8]([CH2:11][CH3:12])CC)C.[C:13]12(N)[CH2:19][CH:17]([CH2:18]1)[CH2:16][CH2:15]C2.[CH2:21](OCC)C>>[CH3:21][C:16]1([CH3:15])[CH:12]2[CH2:18][CH:17]1[CH2:19][CH2:13][CH:11]2[NH:8][C:1](=[O:4])[CH:2]=[CH2:3]

Participants

Reactant 4

HCID 3283Diethyl Ether2×

HCID 8471Triethylamine

HCID 13140Acryloyl chloride

HCID 15730006Bicyclo[3.1.1]heptan-1-amine

Product 1

HCID 19795927N-(6,6-dimethylbicyclo[3.1.1]hept-2-yl)-2-propenamide

Procedure

Following the procedure of Example 3, a solution of acryloyl chloride (4.05 ml, 0.05 mole) in ethyl ether (50 ml) was added dropwise to a cold 5° C. mixture of triethylamine (15.3 ml, 0.11 mole) and norpinylamine (6.96; g, 0.05 mole) in ethyl ether (400 ml). The reaction was allowed to warm to room temperature and stirred for 72 hours. The light tan solid was filtered and washed well with ethyl ether. The solvent and triethylamine were removed, leaving the title product as an oily solid. The structure was confirmed by NMR.