Cyclopentanemethylamine → HCID 19381036, compound

HRID 258301Notes

Reaction equation

HRID 258301 reaction equation
[CH:1]1([CH2:6][NH2:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[CH:9]1[C:22]2[C:21]3([CH2:24][N:25]4[CH2:30][CH2:29][CH:28]([N:31]=[C:32]=[O:33])[CH2:27][CH2:26]4)[CH2:23][CH:14]([C:15]4[C:20]3=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:13]=2[CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[CH:19]1[C:20]2[C:21]3([CH2:24][N:25]4[CH2:30][CH2:29][CH:28]([NH:31][C:32]([NH:7][CH2:6][CH:1]5[CH2:5][CH2:4][CH2:3][CH2:2]5)=[O:33])[CH2:27][CH2:26]4)[CH2:23][CH:14]([C:13]4[C:22]3=[CH:9][CH:10]=[CH:11][CH:12]=4)[C:15]=2[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 80153CyclopentanemethylamineHCID 19381059HCID 19381059, compound

Product 1

HCID 19381036HCID 19381036, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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).

Workup

  1. customat 0° C., the cooling bath was removed
  2. customto reach ambient temperature
  3. stirringAfter stirring for 18 h
  4. additionthe reaction mixture was treated with 1N sodium hydroxide
  5. extractionextracted with methylene chloride (2×50 mL)
  6. washThe combined extracts was washed with 1N sodium hydroxide (2×50 mL) and brine (50 mL)
  7. dry with materialdried (sodium sulfate)
  8. concentrationconcentrated
  9. customto give a tan syrup
  10. customChromatography of this material over silica gel (eluant: 98:2 methylene chloride:methanol) affords a white foam
  11. customThis was triturated with hot ether

Sources & evidence

ORD record
ord-9a21b8dac4d5400eb6a174ee1bc9d910
Source dataset
uspto-grants-1993_11
Patent number
US05266570

Reaction notes

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