Phenethyl bromide → HCID 53783712, compound

HRID 487107Notes

Reaction equation

HRID 487107 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][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[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)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 54260071HCID 54260071, compound

Product 1

HCID 53783712HCID 53783712, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the procedure of Example 3, step 4, 0.307 g (1.64 mmol) of crude trans-1,2,3,4,4a,5,6,10b-octahydrobenz[f]isoquinoline in 8 ml of anhydrous DMF was reacted with 0.249 g (1.80 mmol) of anhydrous potassium carbonate and 0.222 ml (1.64 mmol) of (2-bromoethyl)benzene. Chromatography on flash silica, eluting with 20-50% ethyl acetate/petroleum ether, gave 0.12 g (25%) of the title product as a colourless oil. The hydrochloride salt was made using ethereal hydrogen chloride. Upon evaporation of the solvent the title product hydrochloride was obtained as a white solid, m.p. 277°-283° C. (dec). NMR δ(D2O) 1.54-1.92 (4H, m), 2.72 (2H, m), 2.93-3.00 (3H, m), 3.13-3.26 (3H, m), 3.46 (2H, t), 3.71 (1H, m), 3.84 (1H, m), 7.24-7.28 (3H, m), 7.37-7.44 (6H, m). m/z (CI+, NH3) 292 (M+H)+, 200 (M-CH2Ph)+. Analysis calcd. for C21H26ClN: C, 76.92; H, 7.99; N, 4.27%. Found: C, 76.94; H, 7.98; N, 4.44%.

Workup

  1. washChromatography on flash silica, eluting with 20-50% ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-7ae72f06d6e147a4b4cc220675e50c19
Source dataset
uspto-grants-1994_03
Patent number
US05294618

Reaction notes

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