Allyl bromide → HCID 67942351, compound

HRID 487114Notes

Reaction equation

HRID 487114 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+].[CH2:21](Br)[CH:22]=[CH2:23]>CN(C=O)C>[CH2:23]([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)[CH:22]=[CH2:21]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 54260071HCID 54260071, compound

Product 1

HCID 67942351HCID 67942351, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the procedure of Example 3, step 4, 0.152 g (0.810 mmol) of crude trans-1,2,3,4,4a,5,6,10b-octahydrobenz[f]isoquinoline in 10 ml of anhydrous DMF was reacted with 0.123 g (0.890 mmol) of anhydrous potassium carbonate and 0.074 ml (0.855 mmol) of allyl bromide. Chromatography on flash silica, eluting with 3-7% methanol/dichloromethane, then on alumina, eluting with 2-5% ethyl acetate/petroleum ether, gave 0.064 g (35%) of the title product as a colourless oil. 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. 204°-214° C. NMR δ(D2O) 1.57 (1H, m), 1.69 (1H, m), 1.80-1.92 (2H, m), 2.66-2.77 (2H, m), 2.88-2.95 (3H, m), 3.18 (1H, t, J=11.4 Hz), 3.60 (1 H, m), 3.77 (1H, m), 3.81 (2H, d, J=7.2 Hz), 5.60-5.65 (2H, m), 5.98 (1H, m), 7.22-7.29 (3H, m), 7.35-7.37 (1H, m). m/z (CI+, NH3) 228 (M+H)+. Analysis calcd. for C16H22ClN: C, 72.85; H, 8.41; N, 5.31%. Found: C, 72.84; H, 8.40; N, 5.26%.

Workup

  1. washChromatography on flash silica, eluting with 3-7% methanol/dichloromethane
  2. washon alumina, eluting with 2-5% ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-80a00d2d4bb149948c5b1ee6de2363a1
Source dataset
uspto-grants-1994_03
Patent number
US05294618

Reaction notes

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