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 340679Notes

Reaction equation

HRID 340679 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-1fd2f53bcaa74e27a3b29df0ad093c74
Source dataset
uspto-grants-2014_11
Patent number
US08895591B2

Reaction notes

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