Potassium Carbonate → HCID 22850901, compound

HRID 487111Notes

Reaction equation

HRID 487111 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+].[N+:21]([C:24]1[CH:32]=[CH:31][C:27]([CH2:28][CH2:29]Br)=[CH:26][CH:25]=1)([O-:23])=[O:22]>CN(C=O)C>[N+:21]([C:24]1[CH:32]=[CH:31][C:27]([CH2:28][CH2:29][N:3]2[CH2:2][CH2:1][C@@H:10]3[C@H:5]([CH2:6][CH2:7][C:8]4[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=43)[CH2:4]2)=[CH:26][CH:25]=1)([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 792664-Nitrophenethyl bromideHCID 54260071HCID 54260071, compound

Product 1

HCID 22850901HCID 22850901, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the procedure of Example 3, step 4, 0.300 g (1.60 mmol) of crude trans-1,2,3,4,4a,5,6,10b-octahydrobenz[f]isoquinoline in 10 ml of anhydrous DMF was reacted with 0.244 g (1.77 mmol) of anhydrous potassium carbonate and 0.369 g (1.60 mmol) of 4-nitrophenethyl bromide. Chromatography on flash silica, eluting with 50-100% ethyl acetate/petroleum ether, then on a Lobar column, eluting with 50% ethyl acetate/petroleum ether, afforded 0.200 g (37%) 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. 232°-233° C. (dec). NMR δ(CDCl3) 1.50 (1H, m), 1.86-1.91 (1H, m), 2.28-2.61 (5H, m), 2.86-3.06 (3H, m), 3.24-3.26 (2H, m), 3.49-3.52 (2H, m), 3.66 (1H, m), 3.85 (1H, m), 7.10-7.19 (4H, m), 7.49 (2H, d, J=8.6 Hz), 8.19 (2H, d, J=8.6 Hz). m/z (CI+, NH3) 307 (M-NO+H)+, 200 (M-CH2C6H4NO2)+, 188.

Workup

  1. washChromatography on flash silica, eluting with 50-100% ethyl acetate/petroleum ether
  2. washon a Lobar column, eluting with 50% ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-38caf70899ad4bf488db966df8b21a71
Source dataset
uspto-grants-1994_03
Patent number
US05294618

Reaction notes

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