N-methyl-2-pyrrolidone → 1-(4-(3-(4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl)propoxy)-3-methoxyphenyl)-2-hydroxyethanone

HRID 233944Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:11]3[CH:12]=[CH:13][C:14]([F:16])=[CH:15][C:10]=3[O:9][N:8]=2)[CH2:3][CH2:2]1.Cl[CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:31])[CH2:29][OH:30])=[CH:24][C:23]=1[O:32][CH3:33].C([O-])(O)=O.[Na+].CN1CCCC1=O>O>[F:16][C:14]1[CH:13]=[CH:12][C:11]2[C:7]([CH:4]3[CH2:3][CH2:2][N:1]([CH2:18][CH2:19][CH2:20][O:21][C:22]4[CH:27]=[CH:26][C:25]([C:28](=[O:31])[CH2:29][OH:30])=[CH:24][C:23]=4[O:32][CH3:33])[CH2:6][CH2:5]3)=[N:8][O:9][C:10]=2[CH:15]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-(4-piperidinyl)-6-fluoro-1,2-benzisoxazole (1.3 g, 5.8 mmol), 1-[4-(3-chloropropoxy)-3-methoxyphenyl]-2-hydroxyethanone (1.5 g, 5.8 mmol), NaHCO3 (1.5 g) and 1-methyl-2-pyrrolidinone (50 ml) was stirred under N2 at 100° C. for 6 hours. The reaction was poured into H2O, and the aqueous suspension was extracted with EtOAc. The extract was washed (H)), dried (MgSO4) and concentrated to afford the product.

Workup

extractionthe aqueous suspension was extracted with EtOAc
washThe extract was washed (H)),
dry with materialdried (MgSO4)
concentrationconcentrated
customto afford the product

Sources & evidence

ORD record: ord-c3b5648f52fe4934bedcffad53e3faa4
Source dataset: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05593995

Reaction notes

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