Sodium Hydroxide → 3-[4-(4-Benzyl-phenyl)-piperazin-1-yl]-propionic acid sodium salt

HRID 2353233Notes

Reaction equation

HRID 2353233 reaction equation
Cl.[CH2:2]([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:27])[CH2:24][CH2:25]Br.[OH-].[Na+:29]>>[CH3:21][O:22][C:23](=[O:27])[CH2:24][CH2:25][N:18]1[CH2:19][CH2:20][N:15]([C:12]2[CH:13]=[CH:14][C:9]([CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[CH:10][CH:11]=2)[CH2:16][CH2:17]1.[Na+:29].[CH2:2]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([CH2:25][CH2:24][C:23]([O-:27])=[O:22])[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 76934Methyl 3-bromopropanoateHCID 574195541-(4-Benzyl-phenyl)-piperazine hydrochloride

Product 2

HCID 574195573-[4-(4-Benzyl-phenyl)-piperazin-1-yl]-propionic acid methyl esterYield 42.6%HCID 589025293-[4-(4-Benzyl-phenyl)-piperazin-1-yl]-propionic acid sodium saltYield 89.5%

Procedure

3-[4-(4-Benzyl-phenyl)-piperazin-1-yl]-propionic acid methyl ester (120 mg, 42.6%) was prepared from 1-(4-Benzyl-phenyl)-piperazine hydrochloride (250 mg, 0.77 mmol) and 3-bromo-propionic acid methyl ester (128 mg, 0.77 mmol) using the method described in Example 5. Following the procedure described in Example 2, the ester (120 mg, 0.35 mmol) was treated with 1N NaOH (0.43 mL, 0.43 mmol) to yield the title compound (110 mg, 89.5%): MS (ESI) m/z 325 (M+1); 1H NMR (400 MHz, DMSO-d6) δ 2.02 (t, J=7.6 Hz, 2H), 2.43-2.51 (m, 6H), 3.03 (t, J=4.8 Hz, 4H), 3.81 (s, 2H), 6.83 (d, J=8.8 Hz, 2H), 7.04 (d, J=8.8 Hz, 2H), 7.14-7.19 (m, 3H), 7.26 (m, 2H).

Sources & evidence

ORD record
ord-10bfd1b659ca448aab50f844cf5988c1
Source dataset
uspto-grants-2010_07
Patent number
US07750012B2

Reaction notes

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