Ethanol → [2-(2-Aminoethyl)-4,5-dimethoxyphenyl]acetonitrile

HRID 76325Notes

Reaction equation

[C:1]([CH2:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[CH2:14][CH2:15][NH:16]C(=O)C(F)(F)F)#[N:2].C(O)C.C(=O)([O-])[O-].[K+].[K+]>O>[NH2:2][CH2:1][CH2:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[CH2:14][C:15]#[N:16]

Participants

Conditions

Temperature: 50 °C

Procedure

Heat, at 50° C., a mixture of N-{2-[2-(cyanomethyl)-4,5-dimethoxyphenyl]ethyl}-2,2,2-trifluoroacetamide (20.5 g, 64.8 mmoles), ethanol (160 mL), potassium carbonate (13.2 g, 97.2 mmoles) and water (40 mL). After being in contact for 1 hour 30 minutes, extract the mixture by adding 200 mL of dichloromethane and 100 mL of saturated aqueous NaCl solution. Extract the aqueous phase with 100 mL of dichloromethane. Combine the organic phases, wash them with saturated aqueous NaCl solution (100 mL), dry them over MgSO4 and carry out drying in vacuo to obtain 10 g of a yellow oil corresponding to the title compound.

Workup

extractionextract the mixture
additionby adding 200 mL of dichloromethane and 100 mL of saturated aqueous NaCl solution
extractionExtract the aqueous phase with 100 mL of dichloromethane
washwash them with saturated aqueous NaCl solution (100 mL)
dry with materialdry them over MgSO4
customcarry out drying in vacuo

Sources & evidence

ORD record: ord-1d189e75c9634fadb2e94355772fedd2
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835627B2

Reaction notes

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