Ethanol, reaction products with ammonia, distn. residues → 2-(1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-ylidene)ethanamine

HRID 2389905Notes

Reaction equation

HRID 2389905 reaction equation
[CH2:1]1[C:9]2[C:4](=[N:5][CH:6]=[C:7]3[CH2:12][CH2:11][C:10](=[CH:13][C:14]#[N:15])[C:8]3=2)[O:3][CH2:2]1.N.C(O)C>CO.[Co]>[CH2:1]1[C:9]2[C:4](=[N:5][CH:6]=[C:7]3[CH2:12][CH2:11][C:10](=[CH:13][CH2:14][NH2:15])[C:8]3=2)[O:3][CH2:2]1

Participants

5

Reactant 2

HCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 666019131,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-ylideneacetonitrile

Product 1

HCID 666020482-(1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-ylidene)ethanamine

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridine-8-ylideneacetonitrile (84.9 mg, 0.428 mmol) in methanol (3 mL) were added Raney cobalt (400 mg) and 2M ammonia/ethanol solution (1.5 mL), and the mixture was stirred at room temperature for 4 hr under a hydrogen atmosphere. The catalyst was filtered through celite, and the filtrate was concentrated under reduced pressure to give the title compound. The obtained title compound was used for the reaction in Example 19 without purification.

Workup

  1. filtrationThe catalyst was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5d0c04068aac44738caf062991152808
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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