Homoveratrylamine → HCID 178490341, compound

HRID 617236Notes

Reaction equation

HRID 617236 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][CH:13]3[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH2:20]([NH2:32])[CH2:21][C:22]1[CH:31]=[CH:30][C:27]([O:28][CH3:29])=[C:24]([O:25][CH3:26])[CH:23]=1>C(O)C>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C@H:13]3[CH2:18][CH2:17][C@H:16]([NH:32][CH2:20][CH2:21][C:22]4[CH:31]=[CH:30][C:27]([O:28][CH3:29])=[C:24]([O:25][CH3:26])[CH:23]=4)[CH2:15][CH2:14]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8421HomoveratrylamineHCID 21851602HCID 21851602, compound

Product 1

HCID 178490341HCID 178490341, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

275 mg 4-(7-chloroquinolin-4-ylamino)-cyclohexanone (see Example 124) and 181 mg of homoveratrylamine were boiled at reflux for 3 hours in 5 ml of ethanol in the presence of molecular sieve. The solution, which was cooled and freed from the molecular sieve, was concentrated to dryness. The residue was again taken up in 5 ml of ethanol and treated under argon at +5° C. with 37 mg of sodium borohydride. After 1 hour the mixture was concentrated and the residue was suspended in dichloromethane. The excess reducing agent was decomposed by the addition of 2 ml of 3N sodium hydroxide solution. The mixture was diluted with water and the dichloromethane was separated. The dried organic phase was concentrated. The residue was chromatographed on silica gel with dichloromethane/methanol (3:1). The free base obtained was crystallized as the dihydrochloride by treatment with 3N hydrochloric acid in methanol. Yield: 280 mg (54%) of white crystals, m.p. 210° C.

Workup

  1. temperatureThe solution, which was cooled
  2. concentrationwas concentrated to dryness
  3. additiontreated under argon at +5° C. with 37 mg of sodium borohydride
  4. concentrationAfter 1 hour the mixture was concentrated
  5. additionwas decomposed by the addition of 2 ml of 3N sodium hydroxide solution
  6. additionThe mixture was diluted with water
  7. customthe dichloromethane was separated
  8. concentrationThe dried organic phase was concentrated
  9. customThe residue was chromatographed on silica gel with dichloromethane/methanol (3:1)
  10. customThe free base obtained
  11. customwas crystallized as the dihydrochloride by treatment with 3N hydrochloric acid in methanol

Sources & evidence

ORD record
ord-cb3aac9057ac447293a08aedece09ece
Source dataset
uspto-grants-1999_09
Patent number
US05948791

Reaction notes

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