Cycloheptylamine → N-(2,2-dimethoxyethyl)cycloheptanamine

HRID 909874Notes

Reaction equation

HRID 909874 reaction equation
[CH:1]1([NH2:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:9][O:10][CH:11]([O:14][CH3:15])[CH:12]=O>CO.[Pd]>[CH3:9][O:10][CH:11]([O:14][CH3:15])[CH2:12][NH:8][CH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 2899CycloheptylamineHCID 162650Acetaldehyde, 2,2-dimethoxy-

Product 1

HCID 59224582N-(2,2-dimethoxyethyl)cycloheptanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of cycloheptanamine (8.62 g) in methanol (20 mL) was added 2,2-dimethoxyacetaldehyde (11.49 mL) and the mixture stirred at room temperature for 5 h. Palladium on carbon 10% (1 g) was added and the mixture hydrogenated at 5 bar for 16 h. It was filtered and concentrated under vacuum to give N-(2,2-dimethoxyethyl)cycloheptanamine as an oil (15.26 g). 1H NMR (300 MHz, CDCl3) δ 4.47 (t, J=5.6 Hz, 1H), 3.39 (s, 6H), 2.73 (d, J=5.6 Hz, 2H), 2.67-2.55 (m, 1H), 1.90-1.25 (m, 12H).

Workup

  1. waitthe mixture hydrogenated at 5 bar for 16 h
  2. filtrationIt was filtered
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-38ae95b784f04927b7fd605498ba15dc
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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