Ethanol → HCID 15816945, compound

HRID 1955878Notes

Reaction equation

HRID 1955878 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([O-])([O-])=O.[K+].[K+].S(O[CH2:28][CH2:29][CH:30]1[O:35][C:34]2[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=2[O:32][CH2:31]1)(C)(=O)=O.C(O)C>C(#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]([CH2:28][CH2:29][CH:30]4[O:35][C:34]5[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=5[O:32][CH2:31]4)[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 153801072-Mesyloxyethyl-1,4-benzodioxan

Product 1

HCID 15816945HCID 15816945, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (4.7 g, 21 mmol), K2CO3 (3.5 g, 25.4 mmol) and 2-mesyloxyethyl-1,4-benzodioxan (5.5 g, 21.3 mmol) in acetonitrile (250 ml) was heated at reflux for 3.5 hours. At the end of the reaction, insolubles were filtered. The solid was washed with dichloromethane (200 ml). The solutions were combined and evaporated to an oil. This crude oil was purified by flash chromatography on a silica gel column. The material thus obtained was crystal- lized from ethanol. The 2-[4(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]- ethyl]-1,Sbenzodioxan crystals were collected and weighed 3.8 g, 48%, m.p.=112°-113° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 hours
  3. customAt the end of the reaction, insolubles
  4. filtrationwere filtered
  5. washThe solid was washed with dichloromethane (200 ml)
  6. customevaporated to an oil
  7. customThis crude oil was purified by flash chromatography on a silica gel column
  8. customThe material thus obtained
  9. customThe 2-[4(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]- ethyl]-1,Sbenzodioxan crystals were collected

Sources & evidence

ORD record
ord-b4a68df466c84891b17d2249c706f120
Source dataset
uspto-grants-1998_07
Patent number
US05776963

Reaction notes

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