1-Methylpiperazine → (R)-1-[4-(6-fluoro-benzo[d]isoxazol-3-yl)-phenoxy]-3-(4-methyl-piperazin-1-yl)-propan-2-ol

HRID 852112Notes

Reaction equation

HRID 852112 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.[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]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:10]=[CH:11][C:12]([O:15][CH2:16][C@H:17]([OH:18])[CH2:19][N:26]4[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]4)=[CH:13][CH:14]=3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 531671-MethylpiperazineHCID 58928269(R)-6-fluoro-3-(4-oxiranylmethoxy-phenyl)-benzo[d]isoxazole

Product 1

HCID 9886420(R)-1-[4-(6-fluoro-benzo[d]isoxazol-3-yl)-phenoxy]-3-(4-methyl-piperazin-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 1-methylpiperazine in ethanol essentially as described above in Example 21. Purity by LC/MS=90%, [M+H]+=386. Remaining 10% identified as N(CH3)2 adduct.

Sources & evidence

ORD record
ord-8c5399fbfb674672bdefd0e36bed3e79
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

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