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Phenethyl bromide → (+/-)-6-[4-(1-Phenethyl-piperidin-3-yl)-phenoxy]-nicotinamide

HRID 228209
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반응식

HRID 228209 반응식
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]2[CH:23]=[CH:22][C:11]([O:12][C:13]3[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][N:14]=3)=[CH:10][CH:9]=2)[CH2:3]1.Br[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:25]([N:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]2[CH:9]=[CH:10][C:11]([O:12][C:13]3[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][N:14]=3)=[CH:22][CH:23]=2)[CH2:3]1)[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 68747046(+/-)-6-(4-Piperidin-3-yl-phenoxy)-nicotinamide hydrochloride2회

생성물 1

HCID 59730202(+/-)-6-[4-(1-Phenethyl-piperidin-3-yl)-phenoxy]-nicotinamide수율 64.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Combine 6-(4-piperidin-3-yl-phenoxy)-nicotinamide (compound of example 322) (0.0237 g, 0.0797 mmol), (2-bromoethyl)benzene (0.0108 mL, 0.0791 mmol), and potassium carbonate (0.0237 g, 0.171 mmol) in dimethylformamide (0.96 mL) and stir for 15 min. Then purify the reaction mixture by ion exchange chromatography (SCX resin, methanol→2 M ammonia in methanol) to provide 0.0204 g (64%) of the title compound as an off-white foam: high resolution mass spectrum (electrospray): m/z calc for C25H28N3O2 402.2182, found 402.2182; 1H NMR (methanol-d4): 8.66 (d, 1H, J=2.0 Hz), 8.28 (dd, 1H, J=2.9.8.3 Hz), 7.37 (d, 2H, J=7.8 Hz), 7.33-7.27 (m, 2H), 7.27-7.18 (m, 3H), 7.12 (d, 2H, J=8.3 Hz), 7.01 (d, 1H, J=8.8 Hz), 3.15 (d, 2H, J=11.2 Hz), 2.97-2.85 (m, 3H), 2.73-2.65 (m, 2H), 2.19 (q, 2H, J=11.2 Hz), 2.03-1.74 (m, 3H), 1.59 (dq, 1H, J=4.4, 12.7 Hz).

후처리

  1. customThen purify the reaction mixture by ion exchange chromatography (SCX resin, methanol→2 M ammonia in methanol)

출처 및 근거

ORD 기록
ord-d7687d3318474af78a24c019eac4abfe
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07560463B2

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