Ethanol, reaction products with ammonia, distn. residues → 2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine hydrobromide

HRID 324639Notes

Reaction equation

HRID 324639 reaction equation
N.C(O)C.[Br:5][C:6]1[C:14]2[O:15][CH2:16][CH2:17][C:13]=2[C:12]2/[C:11](=[CH:18]/[C:19]#[N:20])/[CH2:10][CH2:9][C:8]=2[CH:7]=1.[H][H]>[Ni].C(O)C>[BrH:5].[CH2:17]1[CH2:16][O:15][C:14]2[CH:6]=[CH:7][C:8]3[CH2:9][CH2:10][CH:11]([CH2:18][CH2:19][NH2:20])[C:12]=3[C:13]1=2

Participants

6

Reactant 3

HCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 68423466(E)-(4-bromo-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-ylidene)acetonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 220047782-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine hydrobromideYield 93%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Raney nickel (0.4 g, W2) and 4M ammonia/ethanol solution (10 ml) were added to an ethanol (30 ml) suspension of (E)-(4-bromo-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-ylidene)acetonitrile (0.44 g, 1.59 mmols) and stirred in a hydrogen atmosphere (at from 4 to 5 atmospheres) at room temperature for 5 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethanol (50 ml), and 5% palladium-carbon (1 g, containing 50% water) was added thereto and stirred in a hydrogen atmosphere (at ordinary pressure) at room temperature for 4 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain 0.42 g (yield: 93%) of the target compound. This was amorphous.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethanol (50 ml)
  4. addition5% palladium-carbon (1 g, containing 50% water) was added
  5. filtrationThe reaction mixture was filtered
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dc2d90b58c8d4eb1bf6b0cfdc5333fd3
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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