Isopropanol → 4-[3-[4-(6-Fluoro1,2-benzisoxazol-3-yl)-piperidinyl]-2-hydroxy-1-propoxy]phenyl methyl ether

HRID 55670

Reaction equation

HRID 55670 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.O1CC1C[C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=1[O:28][C:29]1[CH:34]=[CH:33]C(OC)=CC=1CC1OC1.C([OH:45])(C)C>>[CH3:27][O:26][C:24]1[CH:25]=[CH:20][C:21]([O:28][CH2:29][CH:34]([OH:45])[CH2:33][N:12]2[CH2:11][CH2:10][CH:9]([C:6]3[C:5]4[CH:15]=[CH:16][C:2]([F:1])=[CH:3][C:4]=4[O:8][N:7]=3)[CH2:14][CH2:13]2)=[CH:22][CH:23]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 199644222,3-Epoxypropyl4-methoxyphenyl ether

Product 1

HCID 184672574-[3-[4-(6-Fluoro1,2-benzisoxazol-3-yl)-piperidinyl]-2-hydroxy-1-propoxy]phenyl methyl ether

Procedure

A mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (4.4 g, 20 mmol) and 2,3-epoxypropyl-4-methoxyphenyl ether (3.7 g, 20.5 mmol) in isopropyl alcohol (80 ml) was heated to reflux for 2 hours. The mixture was cooled and the crystals were collected to yield 6.81 g (85%), m.p.=134°-135° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. temperatureThe mixture was cooled
  4. customthe crystals were collected
  5. customto yield 6.81 g (85%), m.p.=134°-135° C.

Sources & evidence

ORD record
ord-f6d603aa8bbf4ffc9e1026bef1f47c2a
Source dataset
uspto-grants-1997_04
Patent number
US05624927

Linked notes

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