Ethanolamine → HCID 22661647, compound

HRID 392847Notes

Reaction equation

HRID 392847 reaction equation
C(N)CCCCCCCCCCC.[CH2:14]([CH2:16][NH2:17])[OH:15].C=O.[CH2:20]([N:32]1[CH2:37]N(CCCCCCCCCCCC)[CH2:35][N:34]([CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])[CH2:33]1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>C(O)C.CCOCC>[CH2:50]([N:34]1[CH2:35][N:17]([CH2:16][CH2:14][OH:15])[CH2:37][N:32]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:33]1)[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61]

Participants

7

Reactant 4

HCID 700EthanolamineHCID 712Formaldehyde2×HCID 13583DodecylamineHCID 2215931,3,5-Tridodecyl-1,3,5-triazinane

Product 1

HCID 22661647HCID 22661647, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

48 g of dodecylamine (259 mmol) and 1.7 ml of ethanolamine (29 mmol) were dissolved in 100 ml of ethanol, after which 8.6 g of paraformaldehyde (287 mmol) were added and the mixture was stirred. The turbidity caused by 1,3,5-tridodecyl-1,3,5-triazacyclohexane was redissolved every now and again by addition of ether. After about 1 day, all the paraformaldehyde had dissolved. The solvent was then removed on a rotary evaporator, the residue was dissolved in a little toluene and the product was then again freed of solvent under reduced pressure. This left 55 g of a viscous colorless product which, according to NMR spectroscopy, consisted of about 75 mol % of 1,3,5-tridodecyl-1,3,5-triazacyclohexane and 25 mol % of 1,3-didodecyl-5-(2-hydroxyethyl)-1,3,5-triazacyclohexane and a little toluene.

Workup

  1. dissolutionwas redissolved every now and
  2. customThe solvent was then removed on a rotary evaporator
  3. dissolutionthe residue was dissolved in a little toluene

Sources & evidence

ORD record
ord-07bd243e456d44e4bd122d5582b353bf
Source dataset
uspto-grants-2004_10
Patent number
US06803431B1

Reaction notes

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