Ethylenediamine → HCID 68576326, compound

HRID 273069Notes

Reaction equation

HRID 273069 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([C:22]#[N:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:24](N)[CH2:25][NH2:26]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CN1CCCC1=O>[CH3:8][OH:9].[NH3:1].[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([C:22]4[NH:26][CH2:25][CH2:24][N:23]=4)[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 3301EthylenediamineHCID 598373944-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbonitrile

Product 2

HCID 21705897Ammonia methanolHCID 68576326HCID 68576326, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4-[4-(3-Pyrrolidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-carbonitrile (0.5 g, 3.1 mmol), ethylenediamine (1.5 mL, 22 mmol), copper (II) acetate (0.07 g, 0.3 mmol) and N-methylpyrrolidinone (1.5 mL) were combined and subjected to microwave (Smith Personal Synthesiser) irradiation at 220° C. for 1 hour. The reaction mixture was concentrated in vacuo to provide a brown oil. This was columned by flash chromatography on silica gel eluting with dichlromethane:methanol:ammonia (94:6:0.6 to 85:15:1.5) to provide the title compound (0.157 g, 31%) as a yellow oil. LRMS ESI+ m/z 358 [MH]+.

Workup

  1. customsubjected to microwave (Smith Personal Synthesiser) irradiation at 220° C. for 1 hour
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto provide a brown oil

Sources & evidence

ORD record
ord-c0e9231fcdaa4491873d8572353c975f
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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