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 1623884Notes

Reaction equation

HRID 1623884 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 7915Isopropyl AcetateSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-3def9dfa05be47e9a4f3f49257cfa376
Source dataset
uspto-grants-2014_07
Patent number
US08778978B2

Reaction notes

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