5-(4-Fluoro-phenyl)-2,3a,10-trimethyl-1,2,3,3a,4,7-hexahydro-2,7a-diaza-cyclohepta[jk]fluorene → 5-(4-Fluoro-phenyl)-2,3a,10-trimethyl-1,2,3,3a,4,5,6,7-octahydro-2,7a-diaza-cyclohepta[jk]fluorene

HRID 576516Notes

Reaction equation

HRID 576516 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:26][C:13]3([CH3:27])[CH2:14][N:15]([CH3:25])[CH2:16][C:17]4[C:18]5[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][C:23]=5[N:11]([C:12]=43)[CH2:10][CH:9]=2)=[CH:4][CH:3]=1>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:26][C:13]3([CH3:27])[CH2:14][N:15]([CH3:25])[CH2:16][C:17]4[C:18]5[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][C:23]=5[N:11]([C:12]=43)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 533547535-(4-Fluoro-phenyl)-2,3a,10-trimethyl-1,2,3,3a,4,7-hexahydro-2,7a-diaza-cyclohepta[jk]fluorene

Product 1

HCID 533781645-(4-Fluoro-phenyl)-2,3a,10-trimethyl-1,2,3,3a,4,5,6,7-octahydro-2,7a-diaza-cyclohepta[jk]fluorene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(4-Fluoro-phenyl)-2,3a,10-trimethyl-1,2,3,3a,4,7-hexahydro-2,7a-diaza-cyclohepta[jk]fluorene (30 mg, 0.083 mmol) was dissolved in MeOH (4 mL) and the solution was purged with nitrogen. Palladium chloride (15 mg) was added and hydrogen gas was bubbled through the reaction mixture for 2 h. The reaction mixture was filtered through Celite bed and the Celite bed was rinsed with MeOH. The filtrate was concentrated under reduced pressure to obtain 5-(4-fluoro-phenyl)-2,3a,10-trimethyl-1,2,3,3a,4,5,6,7-octahydro-2,7a-diaza-cyclohepta[jk]fluorene. 1H NMR, (HCl, salt, CD3OD) δ (ppm): 7.30 (m, 3H), 7.18 (m, 1H), 7.05-6.95 (m, 3H), 4.70 (m, 2H), 4.30 (m, 2H), 4.10 (m, 1H), 3.58-3.40 (m, 2H), 3.15 (s, 3H), 2.42 (s, 3H), 2.30 (m, 2H), 1.90-1.80 (m, 2JH), 1.70 (s, 3H).

Workup

  1. customthe solution was purged with nitrogen
  2. additionPalladium chloride (15 mg) was added
  3. customhydrogen gas was bubbled through the reaction mixture for 2 h
  4. filtrationThe reaction mixture was filtered through Celite bed
  5. washthe Celite bed was rinsed with MeOH
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b2a0e01a54854d0db3f836d4c2946d6d
Source dataset
uspto-grants-2015_05
Patent number
US09040519B2

Reaction notes

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