Ammonia → {4-[2-(Diethylamino)ethoxy]phenyl}methanamine

HRID 215754

Reaction equation

[CH2:1]([N:3]([CH2:6][CH2:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1)[CH2:4][CH3:5])[CH3:2].[NH3:17]>C(O)C.[Ni]>[CH2:1]([N:3]([CH2:6][CH2:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][NH2:17])=[CH:11][CH:10]=1)[CH2:4][CH3:5])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To the solution of 4-diethylaminoethoxybenzaldehyde X in 180 ml 10% solution of ammonia in anhydrous ethanol, 4.5 g RaNi was added and the mixture was heated to 80° C. at the pressure 68 atm in the autoclave under hydrogen input to the reaction mixture under stirring for 12 hours. The mixture was cooled, the catalyst was filtered off, washed with ethanol. The solvent was distilled off from the solution and the distillation residue was purified by distillation under the reduced pressure. Afforded 13 g (65%) of 4-diethylaminoethoxybenzylamine XI. Colourless fluid 138-140° C./0.5 torr, n20D=1.520. Lit. [6.7] reports 130° C./0.3 torr, n20D=1.5220.

Workup

temperatureThe mixture was cooled
filtrationthe catalyst was filtered off
washwashed with ethanol
distillationThe solvent was distilled off from the solution
distillationthe distillation residue was purified by distillation under the reduced pressure

Sources & evidence

ORD record: ord-854c51b8d09f40c48d3a03ca81d923d3
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193184B2

Linked notes

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