Methanol → HCID 4913174, compound

HRID 1417953Notes

Reaction equation

HRID 1417953 reaction equation
Cl[C:2]1[O:6][N:5]=[C:4]2[C:7]3[C:12]([CH2:13][CH2:14][C:3]=12)=[CH:11][CH:10]=[CH:9][CH:8]=3.[OH:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(Cl)Cl.CO>CN1CCCC1=O.C(Cl)(Cl)Cl.CCOC(C)=O>[OH:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][N:21]([C:2]2[O:6][N:5]=[C:4]3[C:7]4[C:12]([CH2:13][CH2:14][C:3]=23)=[CH:11][CH:10]=[CH:9][CH:8]=4)[CH2:20][CH2:19]1

Participants

8

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 76771-(2-Hydroxyethyl)piperazineHCID 10987412Naphth[1,2-c]isoxazole, 3-chloro-4,5-dihydro-

Product 1

HCID 4913174HCID 4913174, compound

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A stirred mixture of 3-chloro-4,5-dihydronaphth[1,2-c]isoxazole (3.0 g, 14.63 mmol), 1-(2-hydroxyethyl)-piperazine (17.95 ml, 146.3 mmol) and K2O3 (4.1 g, 29.3 mmol) in 18 ml of N-methlypyrrolidinone under N2 was lowered into an oil bath preheated to 150° C. The mixture was heated while stirring under N2 for 1 hour. At that time, TLC (CH2Cl2) showed no remaining starting material. The mixture was removed from the heating bath, allowed to cool to room temperature, and diluted with H2O. Upon the addition of heptane, a solid precipitated. The solid was collected, washed with heptane and H2O, and dried in vacuo (0.1 mm) at 85° C. overnight to provide pure product, mp of 137°-138° C., homogeneous by TLC [silica, 1:1 CH3OH:EtOAc, Rf=0.67]. The IR (CHCl3), NMR (CDCl3) and Mass Spectrum (M+ =299, EI, 70 eV) were consistent with the structure. The yield was 2.603 g (8.70 mmol, 59.47%).

Workup

  1. customwas lowered into an oil bath
  2. custompreheated to 150° C
  3. temperatureThe mixture was heated
  4. customThe mixture was removed from the heating bath
  5. additiondiluted with H2O
  6. additionUpon the addition of heptane
  7. customa solid precipitated
  8. customThe solid was collected
  9. washwashed with heptane and H2O
  10. customdried in vacuo (0.1 mm) at 85° C. overnight
  11. customto provide pure product, mp of 137°-138° C.

Sources & evidence

ORD record
ord-6ae06f99a1ef49eab72a6fedc884439a
Source dataset
uspto-grants-1999_03
Patent number
US05880121

Reaction notes

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