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

HRID 2353233ノート

反応式

HRID 2353233 の反応式
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

参加物

5

反応物 3

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

生成物 2

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

実験手順

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).

出典と根拠

ORDレコード
ord-10bfd1b659ca448aab50f844cf5988c1
出典データセット
uspto-grants-2010_07
特許番号
US07750012B2

反応ノート

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