Methyl 4-bromobutyrate → 4-[4-(4-Phenoxy-phenyl)-piperazin-1-yl]-butyric acid methyl ester

HRID 2353236Notes

Reaction equation

HRID 2353236 reaction equation
Cl.[O:2]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:21][O:22][C:23](=[O:28])[CH2:24][CH2:25][CH2:26]Br>>[CH3:21][O:22][C:23](=[O:28])[CH2:24][CH2:25][CH2:26][N:18]1[CH2:19][CH2:20][N:15]([C:12]2[CH:13]=[CH:14][C:9]([O:2][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[CH:10][CH:11]=2)[CH2:16][CH2:17]1

Participants

3

Reactant 2

HCID 107604Methyl 4-bromobutyrateHCID 448188041-(4-Phenoxyphenyl)piperazine hydrochloride

Product 1

HCID 574195584-[4-(4-Phenoxy-phenyl)-piperazin-1-yl]-butyric acid methyl esterYield 33.2%

Procedure

The title compound (106 mg, 32.6%) was prepared from the compound from step 2, Example 8 (165 mg, 0.9 mmol) and 4-bromo-butyric acid methyl ester (165 mg, 90 mmol) by the procedure described in step 3 of Example 4: MS (ESI) m/z 355 (M+H); 1H NMR (400 MHz, CDCl3) δ 1.84 (m, 2H), 2.36-2.44 (m, 4H), 2.60 (t, J=4.8 Hz, 4H), 3.14 (t, J=4.8 Hz, 4H), 3.68 (s, 3H), 6.89-7.04 (m, 7H), 7.26-7.29 (m, 1H).

Sources & evidence

ORD record
ord-33c7649e522a4c40b19aecafb3ab40d5
Source dataset
uspto-grants-2010_07
Patent number
US07750012B2

Reaction notes

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