Water → 1-(2-{4-[6-Benzyloxy-2-(4-fluoro-phenyl)-naphthalen-1-yloxy]-phenoxy}-ethyl)-azepane

HRID 1513877ノート

反応式

HRID 1513877 の反応式
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17]([O:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)=[C:16]([C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)[CH:15]=[CH:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.[N:37](=[CH:45][CH2:46]Cl)[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]Cl.O>CN(C=O)C.C(OCC)C>[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17]([O:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:46][CH2:45][N:37]3[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)=[CH:24][CH:23]=1)=[C:16]([C:29]1[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=1)[CH:15]=[CH:14]2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

7

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 534452772-(hexamethyleneimino)ethyl chloride HClHCID 575525594-[6-Benzyloxy-2-(4-fluoro-phenyl)-naphthalen-1-yloxy]-phenol

生成物 1

HCID 575525161-(2-{4-[6-Benzyloxy-2-(4-fluoro-phenyl)-naphthalen-1-yloxy]-phenoxy}-ethyl)-azepane収率 66%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

Add sodium hydride (324 mg, 8.0 mmol) into a solution of 4-[6-benzyloxy-2-(4-fluoro-phenyl)-naphthalen-1-yloxy]-phenol (1.18 g, 2.7 mmol) in DMF (10 mL) and stir for 20 minutes at room temperature. Add 2-(hexamethyleneimino)ethyl chloride hydrogen chloride (1.07 g, 5.4 mmol) and stir at room temperature for 12 hours. Add H2O (10 mL) and diethyl ether (100 mL). Separate layers and wash the aqueous layer with diethyl ether (2×50 mL). Combine organic layers, dry with magnesium sulfate and concentrate in vacuo. Purify the residue over silica gel, eluting the material with a step gradient of methanol/dichloromethane (0% to 10%), to obtain 1.0 g of the title compound (66%): mass spectrum (ion spray) m/z=562.3 (M+H).

後処理

  1. washSeparate layers and wash the aqueous layer with diethyl ether (2×50 mL)
  2. dry with materialCombine organic layers, dry with magnesium sulfate
  3. concentrationconcentrate in vacuo
  4. customPurify the residue over silica gel
  5. washeluting the material with a step gradient of methanol/dichloromethane (0% to 10%)

出典と根拠

ORDレコード
ord-747415ac55f2401c8cc595bf32923145
出典データセット
uspto-grants-2012_07
特許番号
US08217032B2

反応ノート

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