Potassium Carbonate → 4-[3-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxybenzonitrile

HRID 233147

反応式

HRID 233147 の反応式
[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+].Br[CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][C:29]=1[O:36][CH3:37]>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]([CH2:24][CH2:25][CH2:26][O:27][C:28]4[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][C:29]=4[O:36][CH3:37])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 104232304-(3-Bromopropoxy)-3-methoxybenzonitrile

生成物 1

HCID 100471134-[3-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxybenzonitrile収率 68.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.0 g, 13.6 mmol), K2CO3 (2.8 g), 4-(3-bromopropoxy)-3-methoxybenzonitrile (4.0 g, 14.8 mmol) in acetonitrile (70 ml) was heated at reflux for 3 hours. At the end of the reaction, the solvent was removed on a rotary evaporator. The organic material was extracted into dichloromethane (250 ml) and the inorganics were filtered off. The dichloromethane solution was concentrated to a crude oil. The purification was done by flash chromatography over a silica gel column (SiO2, 55 g; eluted with dichloromethane, 600 ml; 1% methanol in dichloromethane, 600 ml). The material thus obtained was crystallized from a small amount of dichloromethane. Recrystallization from ethanol (25 ml) provided 3.8 g (68%) of 4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxybenzonitrile as white crystals, m.p.=107°-108° C.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customAt the end of the reaction
  4. customthe solvent was removed on a rotary evaporator
  5. extractionThe organic material was extracted into dichloromethane (250 ml)
  6. filtrationthe inorganics were filtered off
  7. concentrationThe dichloromethane solution was concentrated to a crude oil
  8. customThe purification
  9. washwas done by flash chromatography over a silica gel column (SiO2, 55 g; eluted with dichloromethane, 600 ml; 1% methanol in dichloromethane, 600 ml)
  10. customThe material thus obtained
  11. customwas crystallized from a small amount of dichloromethane
  12. customRecrystallization from ethanol (25 ml)

出典と根拠

ORDレコード
ord-9be2f0bd822547af82a2b49d45fb9e30
出典データセット
uspto-grants-1997_01
特許番号
US05591745

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