Ethanolamine → 2-[(2-Hydroxyethyl)amino]-4,6-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperdin-4-yl)butylamino]-1,3,5-triazine

HRID 1463689Notes

Reaction equation

HRID 1463689 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]2[CH2:18][C:17]([CH3:20])([CH3:19])[N:16]([O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[C:15]([CH3:29])([CH3:28])[CH2:14]2)[N:5]=[C:4]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]2[CH2:40][C:39]([CH3:42])([CH3:41])[N:38]([O:43][CH:44]3[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]3)[C:37]([CH3:51])([CH3:50])[CH2:36]2)[N:3]=1.[CH2:52]([CH2:54][NH2:55])[OH:53].C(=O)(O)[O-].[Na+]>O1CCOCC1>[OH:53][CH2:52][CH2:54][NH:55][C:2]1[N:3]=[C:4]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]2[CH2:36][C:37]([CH3:50])([CH3:51])[N:38]([O:43][CH:44]3[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]3)[C:39]([CH3:42])([CH3:41])[CH2:40]2)[N:5]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]2[CH2:14][C:15]([CH3:29])([CH3:28])[N:16]([O:21][CH:22]3[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]3)[C:17]([CH3:19])([CH3:20])[CH2:18]2)[N:7]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 516892Sodium BicarbonateHCID 225076382,4-Bis[(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-6-chloro-s-triazine

Product 1

HCID 544358902-[(2-Hydroxyethyl)amino]-4,6-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperdin-4-yl)butylamino]-1,3,5-triazineYield 87.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 10.0 g (13.6 mmol) of 2-chloro-4,6-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperdin-4-yl)butylamino]-1,3,5-triazine, 3.3 g (54.6 mmol) of ethanolamine and 30 ml of dioxane is heated at reflux for four hours. The reaction mixture is then poured into 200 ml of saturated aqueous sodium bicarbonate solution. A precipitate forms. The supernatant liquid is decanted, and the precipitate is partitioned between ether (250 ml) and saturated aqueous sodium bicarbonate solution (100 ml). The ether layer is dried over anhydrous magnesium sulfate and evaporated to obtain a glassy material. Purification by flash chromatography on silica gel (4:1 heptane:ethyl acetate) affords 9.0 g (87% yield) of the title compound as a colorless glass.

Workup

  1. temperatureis heated
  2. temperatureat reflux for four hours
  3. customThe supernatant liquid is decanted
  4. customthe precipitate is partitioned between ether (250 ml) and saturated aqueous sodium bicarbonate solution (100 ml)
  5. dry with materialThe ether layer is dried over anhydrous magnesium sulfate
  6. customevaporated
  7. customto obtain a glassy material
  8. customPurification by flash chromatography on silica gel (4:1 heptane:ethyl acetate)

Sources & evidence

ORD record
ord-325a69d268064a0ebaad81d0fc14f579
Source dataset
uspto-grants-1994_04
Patent number
US05300544

Reaction notes

Loading…