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

HRID 2051545Notes

Reaction equation

HRID 2051545 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 sturcture was confirmed by NMR. Analysis calc. for C12H19NO(193.28): Calc.: C, 74.57; H, 9,91; N, 7.24. Found: C, 74.28; H, 9.65; N, 7.15.

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-010d22baa1184c659f6b480277b97ad6
Source dataset
uspto-grants-1991_05
Patent number
US05019597

Reaction notes

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