Hydrochloric Acid → 6-(4-Aminophenoxy)-hexanoic acid methyl ester

HRID 83788

反応式

HRID 83788 の反応式
Cl.[NH2:2][C:3]1[CH:17]=[CH:16][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1.Cl.[CH3:19]O>>[CH3:19][O:14][C:13](=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][O:7][C:6]1[CH:5]=[CH:4][C:3]([NH2:2])=[CH:17][CH:16]=1

参加物

4

反応物 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 66811347HCID 66811347、化合物

生成物 1

HCID 146502966-(4-Aminophenoxy)-hexanoic acid methyl ester収率 43.8%

実験手順

Method-A Through a mixture of 6-(4-aminophenoxy)-hexanoic acid hydrochloride 16 (150 g, 578 mmol) in methanol (3 L) was passed dry HCl gas at 10° C. for 1 hour and refluxed for 48 hours. Methanol (1.5 L) was distilled off, ice water (1 L) was added and the pH adjusted to 7.5 with K2CO3. Crude 17 was extracted into chloroform, washed with 5% NaHCO3 solution, then water, and then dried over Na2SO4 and distilled to give 17 (60 g, 43.8%) as a thick brown syrup. Method-B 6-(4-Nitrophenoxy)-hexanoic acid methyl ester 21 (40 g, 149.81 mmol) was dissolved in dimethyl formamide (200 ml) in a pressure vessel. Raney nickel (20 g) was added and the mixture stirred under an atmosphere of hydrogen (4 kg) for 16 hours. Catalyst was removed by filtration and dimethyl formamide distilled off under vacuum. Crude 17 was purified by column chromatography on silica gel using chloroform as eluant to get pure 17 (28 grams, 78.8%) as a thick brown syrup.

後処理

  1. customat 10° C.
  2. customfor 1 hour
  3. temperaturerefluxed for 48 hours
  4. distillationMethanol (1.5 L) was distilled off
  5. additionice water (1 L) was added
  6. extractionCrude 17 was extracted into chloroform
  7. washwashed with 5% NaHCO3 solution
  8. dry with materialwater, and then dried over Na2SO4
  9. distillationdistilled

出典と根拠

ORDレコード
ord-53b650998968494ea4af0ab1be506de0
出典データセット
uspto-grants-2014_09
特許番号
US08846845B2

関連ノート

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