4-Hydroxybenzoic Acid → 4-hydroxy-benzoic acid, compd. with (2S,4E)-N-methyl-5-[5-(1-methylethoxy)-3-pyridinyl]-4-penten-2-amine (1:1)

HRID 555585

反応式

HRID 555585 の反応式
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH3:11][NH:12][C@H:13]([CH2:15]/[CH:16]=[CH:17]/[C:18]1[CH:19]=[N:20][CH:21]=[C:22]([O:24][CH:25]([CH3:27])[CH3:26])[CH:23]=1)[CH3:14].C(O)(C)C>C(OC(C)C)(=O)C>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH3:11][NH:12][C@H:13]([CH2:15]/[CH:16]=[CH:17]/[C:18]1[CH:19]=[N:20][CH:21]=[C:22]([O:24][CH:25]([CH3:27])[CH3:26])[CH:23]=1)[CH3:14]

参加物

5

反応物 3

HCID 1354-Hydroxybenzoic Acid2 回HCID 3776Isopropanol2 回HCID 9824145Ispronicline

生成物 1

HCID 115524854-hydroxy-benzoic acid, compd. with (2S,4E)-N-methyl-5-[5-(1-methylethoxy)-3-pyridinyl]-4-penten-2-amine (1:1)

試薬・触媒・溶媒 1

HCID 7915Isopropyl Acetate溶媒

実験手順

p-Hydroxybenzoic acid (2.62 g, 19.0 mmol) was added in portions to a stirred solution (2S)-(4E)-N-methyl-5-(5-isopropoxy-3-pyridinyl)-4-penten-2-amine (4.79 g of 93% pure, 19.0 mmol) in isopropyl acetate (50 mL). During the addition, crystallization of salt was evident. After complete addition of the p-hydroxybenzoic acid, the suspension was heated near its boiling point as isopropanol was slowly added. After 15 mL of isopropanol had been added, complete dissolution was obtained. Cooling of the solution to ambient temperature (overnight) resulted in deposition of a crystalline mass, which was collected by suction filtration and air dried (4.03 g). A second crop (0.82 g) was isolated from the concentrated filtrate, by addition of acetone. The two crops of crystals were combined and recrystallized from acetone (50 mL). The solid was collected by suction filtration and dried in the vacuum oven (50° C.) for 18 h. This left 4.24 g (60.0%) of white crystals (98+% pure by both GCMS and LCMS; m.p. 99-101° C.).

後処理

  1. additionDuring the addition, crystallization of salt
  2. temperaturethe suspension was heated near its
  3. additionwas slowly added
  4. dissolutioncomplete dissolution
  5. customwas obtained
  6. customresulted in deposition of a crystalline mass, which
  7. filtrationwas collected by suction filtration and air
  8. customdried (4.03 g)
  9. customA second crop (0.82 g) was isolated from the concentrated filtrate, by addition of acetone
  10. customrecrystallized from acetone (50 mL)
  11. filtrationThe solid was collected by suction filtration
  12. customdried in the vacuum oven (50° C.) for 18 h

出典と根拠

ORDレコード
ord-b703e66c9f7d46429d95d22b6ffc5b02
出典データセット
uspto-grants-2011_11
特許番号
US08053451B2

関連ノート

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