1,4-Dibromo-2-nitrobenzene → HCID 62896872、化合物

HRID 1817893ノート

反応式

HRID 1817893 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].Cl.[NH2:13][CH2:14][C:15]1([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16]1.C(N(CC)C(C)C)(C)C>CN1CCCC1=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:13][CH2:14][C:15]2([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

参加物

5

反応物 3

HCID 770041,4-Dibromo-2-nitrobenzeneHCID 81531DiisopropylethylamineHCID 211096931-(Aminomethyl)cyclopentan-1-ol--hydrogen chloride (1/1)

生成物 1

HCID 62896872HCID 62896872、化合物収率 43%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

The mixture of 2,5-dibromonitrobenzene (Tokyo Kasei Kogyo Co., Ltd., 5.4 g, 19.2 mmol), 1-(aminomethyl)cyclopentanol hydrochloride (J. Med. Chem. 1981, 24, 12-16, 4.3 g, 28.4 mmol) and N,N-diisopropylethylamine (8.4 mL, 48.1 mmol) in 1-methyl-2-pyrrolidinone (32 mL) was microwaved for 30 min at 200° C. The reaction was quenched with water and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 as eluent) to afford the title compound (2.6 g, 43%) as an orange amorphous solid.

後処理

  1. customwas microwaved for 30 min at 200° C
  2. customThe reaction was quenched with water
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 as eluent)

出典と根拠

ORDレコード
ord-42a2a21addcc496abd29a1388410969d
出典データセット
uspto-grants-2009_10
特許番号
US07598393B2

反応ノート

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