Acetonitrile → HCID 15285671, compound

HRID 866222Notes

Reaction equation

HRID 866222 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.[C:17]([O-:20])([O-])=O.[K+].[K+].C1(C)C(S([C:32]2([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:40](=O)[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:33]2=[O:42])(=O)=O)=CC=CC=1.[C:50](#N)C>>[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:50][CH2:40][C:32]4([C:43]5[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=5)[C:33](=[O:42])[C:34]5[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=5)[C:17]4=[O:20])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 184673502-Toluenesulfonyl-2-phenyl-1,3-indandione

Product 1

HCID 15285671HCID 15285671, compound

Procedure

A mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (2.2 g, 10 mmol), K2CO3 (1.6 g, 11.6 mmol) and 2-toluenesulfonyl-2-phenyl-1,3-indandione (4.2 g, 10 mmol) in acetonitrile (50 ml) was heated at reflux for 3 hours. The mixture was cooled and the insolubles were filtered. The solvent was removed on a rotary evaporator. The residue was purified twice using a flash chromatography column (SiO2, 45 g and 40 g; eluted with DCM). The product thus purified was recrystallized from ethanol (30 ml) and isopropyl ether, yield: 2.8 g, m.p. 149°-150° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. temperatureThe mixture was cooled
  4. filtrationthe insolubles were filtered
  5. customThe solvent was removed on a rotary evaporator
  6. customThe residue was purified twice
  7. washa flash chromatography column (SiO2, 45 g and 40 g; eluted with DCM)
  8. customThe product thus purified
  9. customwas recrystallized from ethanol (30 ml) and isopropyl ether, yield: 2.8 g, m.p. 149°-150° C.

Sources & evidence

ORD record
ord-2771b0c1c99d46318ce97e32a7a9289a
Source dataset
uspto-grants-1996_10
Patent number
US05569653

Reaction notes

Loading…