7-(3-chloropropoxy)-3-(hydroxymethyl)chromen-4-one → Abaperidone

HRID 1598022Notes

Reaction equation

HRID 1598022 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10](=[O:18])[C:11]([CH2:16][OH:17])=[CH:12][O:13]2)=[CH:8][CH:7]=1.Cl.[F:20][C:21]1[CH:35]=[CH:34][C:24]2[C:25]([CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[N:26][O:27][C:23]=2[CH:22]=1>CN(C)C=O>[F:20][C:21]1[CH:35]=[CH:34][C:24]2[C:25]([CH:28]3[CH2:29][CH2:30][N:31]([CH2:2][CH2:3][CH2:4][O:5][C:6]4[CH:15]=[C:14]5[C:9]([C:10](=[O:18])[C:11]([CH2:16][OH:17])=[CH:12][O:13]5)=[CH:8][CH:7]=4)[CH2:32][CH2:33]3)=[N:26][O:27][C:23]=2[CH:22]=1

Participants

4

Reactant 2

HCID 108495517-(3-chloropropoxy)-3-(hydroxymethyl)chromen-4-oneHCID 11334359R-56109 hydrochloride

Product 1

HCID 3037308AbaperidoneYield 37.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By the procedure described above, starting from 2.0 g (7.5 mmoles) of 7-(3-chloropropoxy)-3-(hydroxymethyl)chromen-4-one and 1.93 g (7.5 mmoles) of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride, a solid was obtained by crystallization of the crude product from dimethylformamide to yield 1.27 g of 7-[3-[4-(6-fluoro-1,2-benzisoxazole-3-yl)piperidin-1-yl]propoxy]-3-(hydroxymethyl)-chromen-4-one, mp 200°-202° C.

Sources & evidence

ORD record
ord-30fac052f0864b1996774aa3877ea6f2
Source dataset
uspto-grants-1998_04
Patent number
US05736558

Reaction notes

Loading…