Water → 3-[1-(1-Hydroxyhex-6-yl]-4-piperidinyl]-6-fluoro-1,2-benzisoxazole

HRID 1768571

Reaction equation

Cl.[F:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)=[N:8][O:9][C:5]=2[CH:4]=1.C(=O)([O-])[O-].[Li+].[Li+].Cl[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][OH:31].O>CN(C=O)C>[OH:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][N:13]1[CH2:12][CH2:11][CH:10]([C:7]2[C:6]3[CH:16]=[CH:17][C:3]([F:2])=[CH:4][C:5]=3[O:9][N:8]=2)[CH2:15][CH2:14]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride (1g, 3.9 mmol), lithium carbonate (865 mg, 1.7 mmol) and 6-chloro-1-hexanol (534 mg, 3.9 mmol) in 5 ml dry DMF was heated at 100° C. for 48 h. The reaction was poured into water and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate phase was washed with water, brine, dried with sodium sulphate and concentrated in vacuo. The crude product was purified by chromatography on silica gel 60 eluting with ethyl acetate:methanol (9:1, v/v). Concentration of the appropriate fractions afforded 310 mg (25.6%) of 3-[1-(1-hydroxyhex-6-yl)-4-piperidinyl]-6-fluoro-1, 2-benzisoxazole as an oil.

Workup

extractionthe aqueous mixture was extracted with ethyl acetate
washThe ethyl acetate phase was washed with water, brine
dry with materialdried with sodium sulphate
concentrationconcentrated in vacuo
customThe crude product was purified by chromatography on silica gel 60 eluting with ethyl acetate:methanol (9:1

Sources & evidence

ORD record: ord-e842eb7785cb422790b5f8f18349cf51
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05378714

Linked notes

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