Potassium Carbonate → HCID 22850904, compound

HRID 487113Notes

Reaction equation

HRID 487113 reaction equation
[CH2:1]1[C@@H:10]2[C@H:5]([CH2:6][CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=32)[CH2:4][NH:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25]>CN(C=O)C>[CH3:25][C:24]([CH3:26])=[CH:23][CH2:22][N:3]1[CH2:2][CH2:1][C@@H:10]2[C@H:5]([CH2:6][CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=32)[CH2:4]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 54260071HCID 54260071, compound

Product 1

HCID 22850904HCID 22850904, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the procedure of Example 3, step 4, 0.163 g (0.872 mmol) of crude trans-1,2,3,4,4a,5,6,10b-octahydrobenz[f]isoquinoline in 10 ml of anhydrous DMF was reacted with 0.133 g (0.962 mmol) of anhydrous potassium carbonate and 0.106 ml (0.917 mmol) of 4-bromo-2-methyl-2-butene. Chromatography on flash silica, eluting with 3-10% methanol/dichloromethane gave 0.036 g (16%) of the title product as a white solid. The hydrochloride salt was made using ethereal hydrogen chloride. Upon evaporation of the solvent and recrystallisation from ethanol/ethyl acetate, the title product hydrochloride was obtained as a white solid, m.p. 222°-225° C. NMR δ(D2O/CD3CN) 1.56 (1H, m), 1.67 (1H, m), 1.78 (3H, s), 1.86 (3H, s), 1.76-1.92 (2H, m), 2.62-2.73 (2H, m), 2.84 (1H, t, J=12.0 Hz), 2.92-2.94 ( 2H, m), 3.11 (1H, m), 3.53 (1H, m), 3.69 (1H, m), 3.75 (2H, d, J=7.9 Hz), 5.34 (1H, t), 7.22-7.26 (3H, m), 7.32-7.34 (1H, m). m/z (CI+, NH3) 256 (M+H)+, 188 (M-CH2CH=CMe2 +2H)+, 159, 130, 108, 94, 84, 70.

Workup

  1. washChromatography on flash silica, eluting with 3-10% methanol/dichloromethane

Sources & evidence

ORD record
ord-02ae9cc9842d42f891d592bb7bbfa511
Source dataset
uspto-grants-1994_03
Patent number
US05294618

Reaction notes

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