Hydrochloric Acid → 1,3-Bis-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-hydroxypropane dihydrochloride

HRID 1456539Notes

Reaction equation

[O:1]1[CH2:20][CH:2]1[CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:14]3[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:13]=3[O:12][N:11]=2)[CH2:6][CH2:5]1.[F:21][C:22]1[CH:36]=[CH:35][C:25]2[C:26]([CH:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[N:27][O:28][C:24]=2[CH:23]=1.[ClH:37]>C(O)(C)C.C(O)C>[ClH:37].[ClH:37].[F:19][C:17]1[CH:16]=[CH:15][C:14]2[C:10]([CH:7]3[CH2:8][CH2:9][N:4]([CH2:3][CH:2]([OH:1])[CH2:20][N:32]4[CH2:31][CH2:30][CH:29]([C:26]5[C:25]6[CH:35]=[CH:36][C:22]([F:21])=[CH:23][C:24]=6[O:28][N:27]=5)[CH2:34][CH2:33]4)[CH2:5][CH2:6]3)=[N:11][O:12][C:13]=2[CH:18]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A stirred mixture of 1-(2,3-epoxypropyl)-4(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (1.19 g, 4.3 mmol) and 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (0.95 g, 4.3 mmol) in isopropyl alcohol (50 ml) was heated at reflux for 1 hour, then stirred at 65° C. for 16 hours. The solvent was removed on a rotary evaporator. The solid residues were purified by flash chromatography over a silica gel column (SiO2, 35 g, eluted with methylene chloride, DCM, and CH3OH in DCM). The product thus obtained, weighed 2.55 g. This material was dissolved in ethanol and was treated with a solution of HCl (1M in ether). The salt collected weighed 2.35 g, m.p.>270° C. dec.

Workup

temperaturewas heated
temperatureat reflux for 1 hour
customThe solvent was removed on a rotary evaporator
customThe solid residues were purified by flash chromatography over a silica gel column (SiO2, 35 g, eluted with methylene chloride, DCM, and CH3OH in DCM)
customThe product thus obtained
customThe salt collected

Sources & evidence

ORD record: ord-0420594d58e8489da78a9c17bf8f6b8a
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05843949

Reaction notes

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