3-Amino-1-propanol → 1-(3-Hydroxypropylamino)-3-tetradecyloxy-2-propanol

HRID 1104

Reaction equation

HRID 1104 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[CH2:6]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:7]1[O:9][CH2:8]1>C(O)C>[OH:5][CH2:4][CH2:3][CH2:2][NH:1][CH2:8][CH:7]([OH:9])[CH2:6][O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 38190Oxirane, 2-((tetradecyloxy)methyl)-

Product 1

HCID 196946561-(3-Hydroxypropylamino)-3-tetradecyloxy-2-propanolYield 135%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A 300-ml two-necked flask equipped with a stirrer and a dropping funnel was charged with 25.1 g (0.33 mol) of 3-amino-1-propanol and 6.00 g of ethanol, and the contents were heated and stirred at 80° C. in a nitrogen atmosphere. After 9.00 g (33 mmol) of tetradecyl glycidyl ether were added dropwise over 2 hours, the resultant mixture was stirred further for 1 hour. The reaction mixture was poured into 400 ml of ice water and stirred for 1 hour. Crystals formed were then collected by filtration and recrystallized from methanol, thereby obtaining 15.4 g (yield: 92%) of the title compound (IIa-5).

Workup

  1. customA 300-ml two-necked flask equipped with a stirrer and a dropping funnel
  2. temperaturethe contents were heated
  3. stirringstirred for 1 hour
  4. customCrystals formed
  5. filtrationwere then collected by filtration
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-b9a01b6c4e7348f3b4a477b1d53347a8
Source dataset
uspto-grants-1998_03
Patent number
US05723497

Linked notes

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