4-(4-Fluorophenoxy)piperidine → (R)-1-[4-(6-fluoro-benzo[d]isoxazol-3-yl)-phenoxy]-3-[4-(4-fluoro-phenoxy)-piperidin-1-yl]-propan-2-ol

HRID 852122Notes

Reaction equation

HRID 852122 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH2:16][C@H:17]4[CH2:19][O:18]4)=[CH:11][CH:10]=3)=[N:7][O:8][C:4]=2[CH:3]=1.[F:22][C:23]1[CH:35]=[CH:34][C:26]([O:27][CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:25][CH:24]=1>CN(C)C=O.C(O)C>[F:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH2:16][C@H:17]([OH:18])[CH2:19][N:31]4[CH2:30][CH2:29][CH:28]([O:27][C:26]5[CH:34]=[CH:35][C:23]([F:22])=[CH:24][CH:25]=5)[CH2:33][CH2:32]4)=[CH:11][CH:10]=3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 37348964-(4-Fluorophenoxy)piperidineHCID 58928269(R)-6-fluoro-3-(4-oxiranylmethoxy-phenyl)-benzo[d]isoxazole

Product 1

HCID 9826447(R)-1-[4-(6-fluoro-benzo[d]isoxazol-3-yl)-phenoxy]-3-[4-(4-fluoro-phenoxy)-piperidin-1-yl]-propan-2-ol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

The title compound is prepared from a mixture of (R)-6-fluoro-3-(4-oxiranylmethoxy-phenyl)-benzo[d]isoxazole in dimethylformamide and 4-(4-fluoro-phenoxy)-piperidine (Table No.1, SM 5) in ethanol essentially as described above in Example 21. Purity by LC/MS=86%, [M+H]+=481 and 8%, [M+H]+=573.

Sources & evidence

ORD record
ord-cccd97cacbbc46d58b30b2b14a611fe6
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

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