Ethanol, reaction products with ammonia, distn. residues → 2-[2-(4-Phenylbutyl)-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-ylidene]ethanamine

HRID 1039275Notes

Reaction equation

HRID 1039275 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]2[O:12][C:13]3[C:22]4[C:21](=[CH:23][C:24]#[N:25])[CH2:20][CH2:19][C:18]=4[CH:17]=[CH:16][C:14]=3[N:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N.C(O)C>C(O)C.[Co]>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]2[O:12][C:13]3[C:22]4[C:21](=[CH:23][CH2:24][NH2:25])[CH2:20][CH2:19][C:18]=4[CH:17]=[CH:16][C:14]=3[N:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 67355173[2-(4-Phenylbutyl)-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-ylidene]acetonitrile

Product 1

HCID 673533492-[2-(4-Phenylbutyl)-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-ylidene]ethanamine

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 702EthanolSolvent

Procedure

To a solution of [2-(4-phenylbutyl)-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-ylidene]acetonitrile (125 mg, 0.382 mmol) in ethanol (2.4 mL) were added Raney cobalt (1.2 g) and 2N ammonia/ethanol solution (1.2 mL), and the mixture was stirred at room temperature for 3 hr under a hydrogen atmosphere. The catalyst was filtered off using celite, and the filtrate was concentrated under reduced pressure to give the title compound. The obtained title compound was used for the reaction of Examples 6 and 7 without further purification.

Workup

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

Sources & evidence

ORD record
ord-8c78661474cd4626a3329105f9332f67
Source dataset
uspto-grants-2013_10
Patent number
US08552037B2

Reaction notes

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