Reaction #345483

Reaction equation

cyclopentylmethyamine

[(9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)-4-piperidyl]isocyanate hydrochloride

→

title compound

Yield 35.1%

1-[1-(9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl)-4-piperidyl]-3-(cyclopentylmethyl)urea

Yield 35.1%

Solvents

methylene chloride

Conditions

Workup

1. 1
   Otherat 0° C., the cooling bath was removed
2. 2
   Otherto reach ambient temperature
3. 3
   workup.STIRRINGAfter stirring for 18 h
4. 4
   workup.ADDITIONthe reaction mixture was treated with 1N sodium hydroxide
5. 5
   Extractionextracted with methylene chloride (2×50 mL)
6. 6
   WashThe combined extracts was washed with 1N sodium hydroxide (2×50 mL) and brine (50 mL)
7. 7
   Dryingdried (sodium sulfate)
8. 8
   Concentrationconcentrated
9. 9
   Otherto give a tan syrup
10. 10
    OtherChromatography of this material over silica gel (eluant: 98:2 methylene chloride:methanol) affords a white foam
11. 11
    OtherThis was triturated with hot ether

Procedure

To a cold (ice bath) stirred solution of cyclopentylmethyamine (664 mg, 6.70 mmol) in methylene chloride (5 mL) was added [(9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)-4-piperidyl]isocyanate hydrochloride (221 mg, 0.67 mmol). After stirring the resulting mixture for 0.5 h, at 0° C., the cooling bath was removed and the reaction was allowed to reach ambient temperature. After stirring for 18 h, the reaction mixture was treated with 1N sodium hydroxide and extracted with methylene chloride (2×50 mL). The combined extracts was washed with 1N sodium hydroxide (2×50 mL) and brine (50 mL), dried (sodium sulfate), and concentrated to give a tan syrup. Chromatography of this material over silica gel (eluant: 98:2 methylene chloride:methanol) affords a white foam. This was triturated with hot ether to provide the title compound as a white solid (101 mg, 35%), mp 197.0°-8.0° C.; MS(CI): 430 (M+H); NMR (300 MHz,DMSO-d6): 1.05-1.35 (m, 4H), 1.38-1.78(m, 8H), 1.89(quintet, 1H, J=7.3 Hz), 2.20-2.36(m, 2H), 2.45(s, 2H), 2.78-2.95(m, 4H), 3.26-3.42(m, submerged, 3H), 4.30(s, 1H), 5.66(d, 1H, J=7.5 Hz), 5.73(t, 1H, J=5.5 Hz), 6.84-6.99(m, 4H), 7.18(d, 2H, J=6.4 Hz), 7.26(d, 2H, J=6.9 Hz).

Source