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

HRID 2353233노트

반응식

HRID 2353233 반응식
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

참가 물질

5

반응물 3

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

생성물 2

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

실험 절차

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).

출처 및 근거

ORD 기록
ord-10bfd1b659ca448aab50f844cf5988c1
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07750012B2

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