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

HRID 2389916Notes

Reaction equation

HRID 2389916 reaction equation
[CH2:1]1[C:5]2=[C:6]3[C:7]([CH2:10][CH2:11]/[C:12]/3=[CH:13]\[C:14]#[N:15])=[N:8][CH:9]=[C:4]2[O:3][CH2:2]1>N.C(O)C.[Co]>[CH2:1]1[C:5]2=[C:6]3[C:7]([CH2:10][CH2:11]/[C:12]/3=[CH:13]\[CH2:14][NH2:15])=[N:8][CH:9]=[C:4]2[O:3][CH2:2]1

Participants

4

Reactant 1

HCID 59179421(2E)-1,2,6,7-tetrahydro-8H-cyclopenta[b]furo[3,2-d]pyridin-8-ylideneacetonitrile

Product 1

HCID 59179360(2E)-2-(1,2,6,7-tetrahydro-8H-cyclopenta[b]furo[3,2-d]pyridin-8-ylidene)ethanamineYield 99%

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 22020343Ethanol, reaction products with ammonia, distn. residuesSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of (2E)-1,2,6,7-tetrahydro-8H-cyclopenta[b]furo[3,2-d]pyridin-8-ylideneacetonitrile (10.0 mg, 0.054 mmol) and Raney cobalt (100 mg) in 2M ammonia/ethanol (1 mL) was stirred at 50° C. for 3 hr under a hydrogen atmosphere. The catalyst was filtered through celite, and the filtrate was concentrated under reduced pressure to give the title compound (10.0 mg, yield 99%).

Workup

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

Sources & evidence

ORD record
ord-5b1d6f6d68b242f8a1f510c170d54879
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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