Potassium Carbonate → HCID 22850906, compound

HRID 487110Notes

Reaction equation

HRID 487110 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+].[C:21]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Cl)=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22]>CN(C=O)C>[C:21]([C:25]1[CH:26]=[CH:27][C: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:31][CH:32]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 88198Benzene, 1-(chloromethyl)-4-(1,1-dimethylethyl)-HCID 54260071HCID 54260071, compound

Product 1

HCID 22850906HCID 22850906, compoundYield 27%

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 0.243 g (1.76 mmol) of anhydrous potassium carbonate and 0.310 ml (1.60 mmol) of 4-(tert-butyl)benzyl chloride. Chromatography on flash silica, eluting with 10-30% ethyl acetate/petroleum ether and 30-90% ether/petroleum ether, gave 0.142 g (27%) 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. 229°-230° C. (dec). NMR δ(D2O) 1.33 (9H, s), 1.52 (1H, m), 1.65 (1H, m), 1.72-1.84 (2H, m), 2.60-2.72 (2H, m), 2.88-2.94 (2H, m), 3.20 (1H, t of d), 3.51 (1H, m), 3.70 (1H, m), 4.33 (2H, m), 7.21-7.25 (3H, m), 7.30-7.32 (1H, m), 7.47 (2H, d, J=8.4 Hz), 7.61 (2H, d, J=8.3 Hz). m/z (CI+, NH3) 334 (M+H)+, 233, 186 (M-CH2C6H4CMe3)+, 113.

Workup

  1. washChromatography on flash silica, eluting with 10-30% ethyl acetate/petroleum ether and 30-90% ether/petroleum ether

Sources & evidence

ORD record
ord-f826af057bec4b1b87e0b55db6dc7a5b
Source dataset
uspto-grants-1994_03
Patent number
US05294618

Reaction notes

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