N-Benzyl-4-(3,4-dihydro-2,6-naphthyridin-2(1H)-yl)-N-methylcyclohexanamine → 4-(3,4-Dihydro-2,6-naphthyridin-2(1H)-yl)-N-methylcyclohexanamine

HRID 1193365Notes

Reaction equation

HRID 1193365 reaction equation
[CH2:1]([N:8](C)[CH:9]1[CH2:14][CH2:13][CH:12]([N:15]2[CH2:24][CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[N:20][CH:21]=3)[CH2:16]2)[CH2:11][CH2:10]1)C1C=CC=CC=1>CO>[CH2:16]1[C:17]2[C:22](=[CH:21][N:20]=[CH:19][CH:18]=2)[CH2:23][CH2:24][N:15]1[CH:12]1[CH2:13][CH2:14][CH:9]([NH:8][CH3:1])[CH2:10][CH2:11]1

Participants

3

Reactant 1

HCID 66799315N-Benzyl-4-(3,4-dihydro-2,6-naphthyridin-2(1H)-yl)-N-methylcyclohexanamine

Product 1

HCID 667986494-(3,4-Dihydro-2,6-naphthyridin-2(1H)-yl)-N-methylcyclohexanamineYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-Benzyl-4-(3,4-dihydro-2,6-naphthyridin-2(1H)-yl)-N-methylcyclohexanamine (250 mg, 0.746 mmol, 1.0 eq.) was dissolved in MeOH (5 ml) and degassed with N2. Pd(OH)2 (250 mg) was then added and hydrogenation was carried out for 8 hours. After monitoring by TLC, the reaction mixture was filtered over Celite and the filtrate was concentrated under reduced pressure. The crude product so obtained was used in the next stage without being purified further. Yield: 67% (124 mg, 0.506 mmol)

Workup

  1. customdegassed with N2
  2. additionPd(OH)2 (250 mg) was then added
  3. filtrationthe reaction mixture was filtered over Celite
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d8b57fb5cd3944e29a5a6318d232d29c
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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