trans-2-Phenylcyclopropyl isocyanate → HCID 9888980, compound

HRID 2085073Notes

Reaction equation

HRID 2085073 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([NH2:20])=[CH:12][CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:21]1([C@@H:27]2[CH2:29][C@H:28]2[N:30]=[C:31]=[O:32])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[N:1]1([CH2:7][CH2:8][O:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([NH:20][C:31]([NH:30][CH:28]3[CH2:29][CH:27]3[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:32])=[CH:12][CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 255285trans-2-Phenylcyclopropyl isocyanateHCID 110439124-(2-Morpholinoethoxy)naphthalen-1-amine

Product 1

HCID 9888980HCID 9888980, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl amine (165 mg, 0.61 mmol, 1 equiv.) dissolved in 2.5 mL anhydrous THF was added, via syringe, trans-2-phenyl-cyclopropyl-isocyanate (90 uL, 0.60 mmol, 1 equiv.). The mixture was left stirring at room temperature for 18 h under inert atmosphere, then the solvent was removed in vacuo. The product was purified by column chromatography on SiO2, using 2-4% MeOH in EtOAc as eluent. A taupe foam was isolated, which recrystallized from hot acetonitrile to afford the title compound as a white solid (60 mg), mp 156-157° C.

Workup

  1. additionwas added, via syringe
  2. waitThe mixture was left
  3. customthe solvent was removed in vacuo
  4. customThe product was purified by column chromatography on SiO2
  5. customA taupe foam was isolated
  6. customwhich recrystallized from hot acetonitrile

Sources & evidence

ORD record
ord-e78feceb04bd4e2d8664ce8eff403e6c
Source dataset
uspto-grants-2004_04
Patent number
US06720321B2

Reaction notes

Loading…