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

HRID 5496

Reaction equation

HRID 5496 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

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 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.

Workup

  1. filtrationThe light tan solid was filtered
  2. washwashed well with ethyl ether
  3. customThe solvent and triethylamine were removed

Sources & evidence

ORD record
ord-0c853584f40147fcac7748a5dc4bc09f
Source dataset
uspto-grants-1993_09
Patent number
US05244899

Linked notes

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