3-Methoxypropylamine → N-(3-hexadecyloxy-2-hydroxypropyl)-N-3-methoxypropylamine
Reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH2:6].[CH2:7]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:8]1[O:10][CH2:9]1>C(O)C>[CH2:12]([O:11][CH2:7][CH:8]([OH:10])[CH2:9][NH:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a 2-l flask equipped with a stirrer, a dropping funnel, a nitrogen gas inlet tube and a distillation apparatus, 743.2 g (8.34 mol) of 3-methoxypropylamine (5-a) and 150 ml of ethanol were charged, followed by the dropwise addition of 165.9 g (0.56 mol) of hexadecyl glycidyl ether (4-a) over 3 hours while stirring under heating to 80° C. in a nitrogen atmosphere. After the completion of the dropwise addition, stirring was conducted for further 2 hours at 80° C. From the reaction mixture, ethanol and excessive 3-methoxypropylamine were distilled off by heating under reduced pressure. The residue was purified by chromatography on a silica gel column, whereby 196.5 g of the title compound (6-a) were obtained in the form of a white solid (yield: 91% relative to hexadecyl glycidyl ether).
Workup
- customTo a 2-l flask equipped with a stirrer, a dropping funnel, a nitrogen gas inlet tube
- additionAfter the completion of the dropwise addition
- stirringstirring
- distillationFrom the reaction mixture, ethanol and excessive 3-methoxypropylamine were distilled off
- temperatureby heating under reduced pressure
- customThe residue was purified by chromatography on a silica gel column
Sources & evidence
- ORD record
- ord-93929dd4990d4a7a802e14761a0eb6b4
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05753707
Reaction notes
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