Atropic acid → HCID 86749173, compound

HRID 2260644Notes

Reaction equation

HRID 2260644 reaction equation
[C:1]1([C:7](=[CH2:11])[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:12][C:13]1[CH:27]=[CH:26][C:16]2[C:17]([CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)=[N:18][O:19][C:15]=2[CH:14]=1>C(O)(C)C>[F:12][C:13]1[CH:27]=[CH:26][C:16]2[C:17]([CH:20]3[CH2:21][CH2:22][N:23]([C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)([CH3:11])[C:8]([OH:10])=[O:9])[CH2:24][CH2:25]3)=[N:18][O:19][C:15]=2[CH:14]=1

Participants

4

Reactant 2

HCID 68114Atropic acidHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

Product 1

HCID 86749173HCID 86749173, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-phenylacrylic acid (1.8 g, 12 mmol) and 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (2.4 g, 11 mmol) in 100 ml dry isopropanol was refluxed for 3 h. The mixture was concentrated in vacuo and taken up in water whereupon NaHCO3 was added until pH 8-9. The formed crystals were isolated, washed with ethyl acetate and dried to give 2.0 g 3-(4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidino-2-phenylpropanoic acid. M.p. 194°-200° C.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionwas added until pH 8-9
  3. customThe formed crystals were isolated
  4. washwashed with ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-47fe601903bf4a61a9c0cde148f4a30f
Source dataset
uspto-grants-1995_12
Patent number
US05478845

Reaction notes

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