Triphenylphosphine → 3-{4-[3-(4-Ethoxylphenoxy)propyl]piperazin-1-yl}-6-chloropyridazine

HRID 80740

反応式

HRID 80740 の反応式
[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][OH:17])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[O:18]([C:21]1[CH:26]=[CH:25][C:24](O)=[CH:23][CH:22]=1)[CH2:19][CH3:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[O:18]([C:21]1[CH:26]=[CH:25][C:24]([O:17][CH2:16][CH2:15][CH2:14][N:11]2[CH2:12][CH2:13][N:8]([C:5]3[N:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH2:9][CH2:10]2)=[CH:23][CH:22]=1)[CH2:19][CH3:20]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 121504-EthoxyphenolHCID 5462977Diethyl azodicarboxylateHCID 867627983-[4-(6-Chloropyridazin-3-yl)piperazin-1-yl]propan-1-ol

生成物 1

HCID 510035623-{4-[3-(4-Ethoxylphenoxy)propyl]piperazin-1-yl}-6-chloropyridazine収率 23.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3-[4-(6-chloropyridazin-3-yl)piperazin-1-yl]propan-1-ol (0.77 g, 3 mmol), p-ethoxylphenol (0.41 g, 3 mmol), triphenylphosphine (0.79 g, 3 mmol) and anhydrous THF (20 mL) were placed in a 100 mL three-necked bottle, and DEAD (0.52 g, 3 mmol) was added slowly in dropwise within 10 min under an ice-bath condition. The mixture was stirred at room temperature overnight, subjected to a column chromatography (eluting agent: petroleum/ethyl acetate, v/v 3: 2) to obtain a white solid, 0.27 g, yield 23.9%. mp: 125-127° C.; 1H-NMR (400 MHz, CDCl3, δppm) δ1.39(t, 3H, J=7.2 Hz), 2.00(m, 2H), 2.61(br, 6H), 3.67(br, 4H), 3.98 (m, 4H), 6.83(s, 4H), 6.90(d, 1H, J=9.6 Hz), 7.21(d, 1H, J=9.6 Hz); EI-MS(m/z): 376.2[M+H].

後処理

  1. additionwas added slowly in dropwise within 10 min under an ice-bath condition
  2. washsubjected to a column chromatography (eluting agent: petroleum/ethyl acetate, v/v 3: 2)
  3. customto obtain a white solid, 0.27 g, yield 23.9%

出典と根拠

ORDレコード
ord-e3f47881de454df681c920a9ccaf3483
出典データセット
uspto-grants-2014_09
特許番号
US08846678B2

関連ノート

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