HCID 23353490, compound → HCID 18967546, compound

HRID 235142Notes

Reaction equation

HRID 235142 reaction equation
C([N:8](CC1C=CC=CC=1)[C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2[C:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH:20]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>C(O)(=O)C.[OH-].[Pd+2].[OH-]>[NH2:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2[CH:19]2[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]2)=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 23353490HCID 23353490, compound

Product 1

HCID 18967546HCID 18967546, compoundYield 33.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 176Acetic AcidSolvent

Procedure

A mixture of 7-dibenzylamino-1-(1-methyl-1,2,5,6-tetrahydropyrid-4-yl)-naphthalene (2.85 g, 6.81 mmol) and palladium hydroxide (20% on carbon, 2.06 g) in glacial acetic acid (60 mL) was hydrogenated 22 hours (starting pressure approximately 50 psi). Additional palladium hydroxide (1 g) was added and hydrogenation was continued 13 hours more. The reaction was filtered through celite. The filtrate was neutralized with 4N sodium hydroxide and extracted with methylene chloride. This organic phase was washed with brine, dried and concentrated to 1.3 g of brown oil. Crystallization from isopropanol gave 0.544 g (33%) of 7-amino-1-(1-methyl-4-piperidinyl)-naphthalene as light brown crystals. mp 169.5°-171° C. Analysis calculated for C16H20N2 ; C, 79.96; H, 8.39; N, 11.66. Found: C, 80.14; H, 8.42; N, 11.52.

Workup

  1. waithydrogenation was continued 13 hours
  2. filtrationThe reaction was filtered through celite
  3. extractionextracted with methylene chloride
  4. washThis organic phase was washed with brine
  5. customdried
  6. concentrationconcentrated to 1.3 g of brown oil
  7. customCrystallization from isopropanol

Sources & evidence

ORD record
ord-97c6eeebcc374c6f813bfab68ddd86b9
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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