Morpholine → HCID 19768354, compound

HRID 1590954Notes

Reaction equation

HRID 1590954 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH2:26][CH2:27][CH2:28][CH3:29])[CH:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[N:12]([O:17][CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[C:11]([CH3:25])([CH3:24])[CH2:10]2)[N:5]=[C:4]([N:30]([CH2:48][CH2:49][CH2:50][CH3:51])[CH:31]2[CH2:36][C:35]([CH3:38])([CH3:37])[N:34]([O:39][CH:40]3[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]3)[C:33]([CH3:47])([CH3:46])[CH2:32]2)[N:3]=1.[NH:52]1[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH:40]1([O:39][N:34]2[C:33]([CH3:47])([CH3:46])[CH2:32][CH:31]([N:30]([CH2:48][CH2:49][CH2:50][CH3:51])[C:4]3[N:5]=[C:6]([N:8]([CH2:26][CH2:27][CH2:28][CH3:29])[CH:9]4[CH2:10][C:11]([CH3:24])([CH3:25])[N:12]([O:17][CH:18]5[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]5)[C:13]([CH3:15])([CH3:16])[CH2:14]4)[N:7]=[C:2]([N:52]4[CH2:57][CH2:56][O:55][CH2:54][CH2:53]4)[N:3]=3)[CH2:36][C:35]2([CH3:37])[CH3:38])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 14798Sodium HydroxideHCID 15218751HCID 15218751, compound

Product 1

HCID 19768354HCID 19768354, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 10.0 g (13.7 mmol) of 2-chloro-4,6-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-1,3,5-triazine (see Example 75), 1.43 g (16.4 mmol) of morpholine, 0.8 g of sodium hydroxide, and 30 g of toluene is heated at reflux for four hours. Water is collected in a Dean-Stark trap. The liquid phase is decanted and residual solids are washed with toluene. The combined organic solutions are dried over magnesium sulfate and concentrated to give a viscous oil. Purification by HPLC (Waters Prep. 500 A, 29:1 heptane:ethyl acetate) affords 5.9 g (55% yield) of the title compound, a white powder, m.p. 159°-63° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for four hours
  3. customWater is collected in a Dean-Stark trap
  4. customThe liquid phase is decanted
  5. washresidual solids are washed with toluene
  6. dry with materialThe combined organic solutions are dried over magnesium sulfate
  7. concentrationconcentrated
  8. customto give a viscous oil
  9. customPurification by HPLC (Waters Prep. 500 A, 29:1 heptane:ethyl acetate)

Sources & evidence

ORD record
ord-368c65664f9c4d1d94155c85ea271d5b
Source dataset
uspto-grants-1993_04
Patent number
US05204473

Reaction notes

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