Benzyl Bromide → HCID 54124531, compound

HRID 487106Notes

Reaction equation

HRID 487106 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)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C>[CH2:21]([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)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 54260071HCID 54260071, compound

Product 1

HCID 54124531HCID 54124531, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the procedure of Example 3, step 4, 40.0 mg (0.214 mmol) of trans-1,2,3,4,4a,5,6,10b-octahydrobenz[f]isoquinoline in anhydrous DMF (2 ml) was reacted with 32.5 mg (0.235 mmol) of anhydrous potassium carbonate and 25.4 ml (0.214 mmol) of benzyl bromide. Chromatography on flash silica, eluting with 10-15% ethyl acetate/petroleum ether, gave 32.0 mg (54%) of the title product as a white solid. 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. 244°-248° C. (dec). NMR δ(D2O) 1.49-1.84 (4H, m), 2.68 (2H, m), 2.89-2.99 (3H, m), 3.23 (1H, m), 3.53 (1H, m), 3.73 (1H, m), 4.37 (2H, m), 7.23-7.27 (3H, m), 7.33 (1H, m), 7.54 (5H, s). m/z (CI+, NH3) 278 (M+H)+, 186 (M-CH2Ph)+, 184, 110.

Workup

  1. washChromatography on flash silica, eluting with 10-15% ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-92d814db99fb4c5494331b6846f4d1f9
Source dataset
uspto-grants-1994_03
Patent number
US05294618

Reaction notes

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