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

HRID 267067Notes

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 (H2O), dried (MgSO4O and concentrated to afford the product.

Workup

extractionthe aqueous suspension was extracted with EtOAc
washThe extract was washed (H2O)
dry with materialdried (MgSO4O
concentrationconcentrated
customto afford the product

Sources & evidence

ORD record: ord-1cc591c34a2449b7baeda6ec21c0cb74
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05652241

Reaction notes

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