Dichloromethane → HCID 86753856, compound

HRID 1417958Notes

Reaction equation

HRID 1417958 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]=[C:9]([O:15][CH3:16])[CH:8]=3.[C:17]([O-:20])([O-])=O.[K+].[K+].[CH2:23]([Cl:25])Cl.CC[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].C[N:34]1[CH2:38][CH2:37][CH2:36][C:35]1=O>C(Cl)(Cl)Cl.CCOC(C)=O>[Cl:25][C:23]1[CH:28]=[CH:29][C:30]([C:17]2([OH:20])[CH2:37][CH2:38][N:34]([N:5]3[C:4]4[C:7]5[C:12]([CH2:13][CH2:14][C:3]=4[CH2:2][O:6]3)=[CH:11][CH:10]=[C:9]([O:15][CH3:16])[CH:8]=5)[CH2:35][CH2:36]2)=[CH:31][CH:32]=1

Participants

8

Reactant 5

HCID 6344DichloromethaneHCID 8900HeptaneHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 54295927HCID 54295927, compound

Product 1

HCID 86753856HCID 86753856, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred mixture of 3-chloro-8-methoxy-4,5-dihydronaphth[1,2-c]isoxazole (2.0 g, 8.51 mmol), 4-(p-chlorophenyl)-4-hydroxy-dipiperidine (3.6 g, 17.02 mol) and K2CO3 (2.35 g, 17.02 mmol) in 6 ml of N-methylpyrrolidinone 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 and allowed to cool to room temperature. Upon dilution of the reaction mixture with H2O, a solid precipitated which was recrystallized from EtOAc and dried in vacuo (0.1 mm) at 85° C. to provide pure product, mp of 174°-177° C., homogeneous by TLC [silica, 2:1 heptane:EtOAc, Rf=0.263]. The IR (CHCl3), NMR (CDCl3) and Mass Spectrum (M+ =410, E.I., 70 eV) were consistent with the structure. The yield was 2.3798 g (5.60 mmol, 68.20%).

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. customUpon dilution of the reaction mixture with H2O, a solid precipitated which
  6. customwas recrystallized from EtOAc
  7. customdried in vacuo (0.1 mm) at 85° C.
  8. customto provide pure product, mp of 174°-177° C.

Sources & evidence

ORD record
ord-69436074766e46d0a4fcef2a2f8eefd3
Source dataset
uspto-grants-1999_03
Patent number
US05880121

Reaction notes

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