Propylene Oxide → HCID 10802539, compound

HRID 1768573Notes

Reaction equation

HRID 1768573 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.[CH2:17]1[O:20][CH:18]1[CH3:19]>C(#N)C>[OH:20][CH:18]([CH3:19])[CH2:17][N:12]1[CH2:11][CH2:10][CH:9]([C:6]2[C:5]3[CH:15]=[CH:16][C:2]([F:1])=[CH:3][C:4]=3[O:8][N:7]=2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 6378Propylene OxideHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

Product 1

HCID 10802539HCID 10802539, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazol (1.5 g, 6.8 mmol) and propylene oxide; (2 g, 34.4 mmol) in 25 ml acetonitrile was heated to 50° C. in an autoclave for 3 days. The cooled reaction was concentrated in vacuo and purified by chromatography on silica gel 60 eluting with ethyl acetate:methanol (9:1, v/v). Concentration of the appropriate fraction afforded 1.3 g (68.4%) of 3-[1-(2-hydroxyprop-1-yl)-4-piperidinyl]-6-fluoro-1, 2-benzisoxazole. M.p. 45°-47° C. MS (70 eV): m/z 278 (M+, 18%), 233 (100), 190 (28), 109 (12), 96 (70), 82 (25), 68 (14), 55 (22).

Workup

  1. customThe cooled reaction
  2. concentrationwas concentrated in vacuo
  3. custompurified by chromatography on silica gel 60 eluting with ethyl acetate:methanol (9:1

Sources & evidence

ORD record
ord-b9edd867c98f462492bb27b65bb9d7d3
Source dataset
uspto-grants-1995_01
Patent number
US05378714

Reaction notes

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