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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2389906Generated: October 30, 2026

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

https://huagongshe.com/reaction/2389906

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthanol, reaction products with ammonia, distn. residuesHCID 22020343—
Reactant1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-ylideneacetonitrileHCID 66601913—
CatalystCobaltHCID 104730—
SolventEthanolHCID 702—
Product2-(1,6,7,8-tetrahydro-2H-cyclopenta[d]furo[2,3-b]pyridin-8-yl)ethanamineHCID 59179405—

Reaction Steps

To a solution of 1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-ylideneacetonitrile (500 mg, 2.52 mmol) in ethanol (16 mL) were added Raney cobalt (1 g) and 2M ammonia/ethanol solution (8 mL), and the mixture was stirred at room temperature for 30 hr under a hydrogen atmosphere. The catalyst was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in methanol (20 mL), palladium-carbon powder (100 mg) was added, and the mixture was stirred at room temperature for 12 hr under a hydrogen atmosphere. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound. The obtained title compound was used for the reaction in Examples 25, 26, 27 and 28 without purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08273761B2
Source datasetuspto-grants-2012_09
ORD IDord-98e3088264df4f27854ffb5b0ec7fe55
Source noteuspto-grants-2012_09