2,4-Bis[(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-6-chloro-s-triazine → N-{4,6-Bis[(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-1,3,5-triazin-2-yl}-6-aminohexanoic acid

HRID 1463702Notes

Reaction equation

HRID 1463702 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.[NH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][C:58]([O-:60])=[O:59].[Na+]>COCCOCCOC>[CH:44]1([O:43][N:38]2[C:37]([CH3:51])([CH3:50])[CH2:36][CH:35]([CH2:34][CH2:33][CH2:32][CH2:31][NH:30][C:4]3[N:5]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]4[CH2:14][C:15]([CH3:28])([CH3:29])[N:16]([O:21][CH:22]5[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]5)[C:17]([CH3:19])([CH3:20])[CH2:18]4)[N:7]=[C:2]([NH:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][C:58]([OH:60])=[O:59])[N:3]=3)[CH2:40][C:39]2([CH3:42])[CH3:41])[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]1

Participants

4

Reactant 2

HCID 225076382,4-Bis[(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-6-chloro-s-triazineHCID 23663648hexanoic acid, 6-amino-, monosodium salt

Product 1

HCID 67849678N-{4,6-Bis[(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-1,3,5-triazin-2-yl}-6-aminohexanoic acidYield 69.5%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 20.0 g (27.3 mmol) of 2-chloro-4,6-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-1,3,5-triazine, 25.1 g (0.164 mol) of sodium 6-aminohexanoate, and 200 ml of diglyme is heated at 140° C. for seven hours. The reaction mixture is partitioned between 1N HCl (500 ml) and ether (400 ml), and the aqueous phase is extracted with ether (200 ml). The combined organic layers are washed with water (2×200 ml) and saturated aqueous sodium chloride solution (200 ml), and then dried over anhydrous magnesium sulfate, and finally concentrated to obtain a glass. Purification by flash chromatography on silica gel (2:1 heptane:ethyl acetate) affords 15.7 g (69% yield) of the title compound as a white powdery glass.

Workup

  1. customThe reaction mixture is partitioned between 1N HCl (500 ml) and ether (400 ml)
  2. extractionthe aqueous phase is extracted with ether (200 ml)
  3. washThe combined organic layers are washed with water (2×200 ml) and saturated aqueous sodium chloride solution (200 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationfinally concentrated
  6. customto obtain a glass
  7. customPurification by flash chromatography on silica gel (2:1 heptane:ethyl acetate)

Sources & evidence

ORD record
ord-ce981dc1c36c4d8296d8210347fb73e1
Source dataset
uspto-grants-1994_04
Patent number
US05300544

Reaction notes

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