Ammonia → HCID 58999625, compound

HRID 1593623Notes

Reaction equation

HRID 1593623 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH:7]([CH2:15][C:16]#[N:17])[CH2:6][C:5]2=1.N>C(O)C.[Rh]>[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH:7]([CH2:15][CH2:16][NH2:17])[CH2:6][C:5]2=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 58999618HCID 58999618, compound

Product 1

HCID 58999625HCID 58999625, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (6-fluoro-2,3,4,9-tetrahydro-1H-carbazol-3-yl)acetonitrile (0.423 g, 1.857 mmol) in ethanol (55 mL) kept under nitrogen was added concentrated aqueous ammonia (38 mL) followed by 5% rhodium on alumina catalyst (40% by weight). The mixture was hydrogenated at room temperature and 50 psi for 24 hours. Following TLC, additional catalyst (1.130 g) was added and the hydrogenation was resumed. After 6 hours the catalyst was filtered off over Celite, the cake washed with ethanol and the filtrate evaporated to dryness at reduced pressure. The residue was treated with a small amount of ethanol and evaporated. The procedure was performed three times. The residual oil was purified by flash chromatography on silica gel Merck-60 using a gradient from 2:248 to 10:90 of ammonia saturated methanol in dichloromethane. The desired title compound was obtained as a pale yellow foam (0.405 g). MS (ES): [M−H]− @231.1.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationAfter 6 hours the catalyst was filtered off over Celite
  3. washthe cake washed with ethanol
  4. customthe filtrate evaporated to dryness at reduced pressure
  5. additionThe residue was treated with a small amount of ethanol
  6. customevaporated
  7. customThe residual oil was purified by flash chromatography on silica gel Merck-60

Sources & evidence

ORD record
ord-5d3272dd41d74a618732fbc10282a352
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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