Methyl bromoacetate → 2-[4-(4-Phenoxy-phenyl)-piperazin-1-yl]-acetic acid methyl ester

HRID 2353239Notes

Reaction equation

HRID 2353239 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.Br[CH2:22][C:23]([O:25][CH3:26])=[O:24]>>[CH3:26][O:25][C:23](=[O:24])[CH2:22][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 60984Methyl bromoacetateHCID 448188041-(4-Phenoxyphenyl)piperazine hydrochloride

Product 1

HCID 574195622-[4-(4-Phenoxy-phenyl)-piperazin-1-yl]-acetic acid methyl esterYield 41%

Procedure

The title compound (135 mg, 41%) was prepared from 1-(4-Phenoxy-phenyl)-piperazine hydrochloride. (165 mg, 0.9 mmol) and methyl 2-bromo-acetate (140 mg, 0.92 mmol) by the procedure described in step 3 of Example 6 MS (ESI) m/z 327 (M+H); 1H NMR (400 MHz, CDCl3) δ 2.76 (b, 2.67), 3.21 (t, J=3.2 Hz, 4H), 3.29 (s, 2H), 3.75 (s, 3H), 6.92-7.05 (m, 7H), 7.29 (m, 2H).

Sources & evidence

ORD record
ord-3d998938f11f4842937120ebd8a5e576
Source dataset
uspto-grants-2010_07
Patent number
US07750012B2

Reaction notes

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