Water → 1'-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,5-triazin-2-yl]-1,4'-bipiperidinyl-3-ol

HRID 2175088Notes

Reaction equation

HRID 2175088 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Cl[C:8]1[N:13]=[CH:12][N:11]=[C:10]([N:14]2[CH2:19][CH2:18][CH:17]([N:20]3[CH2:25][CH2:24][CH2:23][CH:22]([OH:26])[CH2:21]3)[CH2:16][CH2:15]2)[N:9]=1.CC1(C)C(C)(C)OB([C:35]2[CH:44]=[CH:43][C:42]3[C:41]([CH3:46])([CH3:45])[CH2:40][CH2:39][C:38]([CH3:48])([CH3:47])[C:37]=3[CH:36]=2)O1.O>C1(C)C=CC=CC=1.C(O)C.O>[CH3:45][C:41]1([CH3:46])[CH2:40][CH2:39][C:38]([CH3:48])([CH3:47])[C:37]2[CH:36]=[C:35]([C:8]3[N:13]=[CH:12][N:11]=[C:10]([N:14]4[CH2:19][CH2:18][CH:17]([N:20]5[CH2:25][CH2:24][CH2:23][CH:22]([OH:26])[CH2:21]5)[CH2:16][CH2:15]4)[N:9]=3)[CH:44]=[CH:43][C:42]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 112439294,4,5,5-Tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolaneHCID 532524851-[1-(4-Chloro-1,3,5-triazin-2-yl)piperidin-4-yl]piperidin-3-ol

Product 1

HCID 532504051'-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,5-triazin-2-yl]-1,4'-bipiperidinyl-3-ol

Reagents, catalysts & solvents 1

HCID 86587398Ethanol toluene waterSolvent

Conditions

Temperature
90 °C

Procedure

45 mg (0.42 mmol) of sodium carbonate are added to 50 mg (0.17 mmol) of 1′-(4-chloro-1,3,5-triazin-2-yl)-1,4′-bipiperidinyl-3-ol and 139 mg (0.42 mmol) of 4,4,5,5-tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolane in 3.2 ml of toluene/ethanol/water (3.2/3.2/1). The reaction mixture is degassed a number of times, and 19 mg (0.017 mmol) of tetrakis-(triphenylphosphine)palladium(0) are added under nitrogen atmosphere, the mixture is treated in an ultrasound bath for 10 min and subsequently heated at 90° C. for 5 h. Water is added to the reaction mixture, which is then extracted three times with ethyl acetate/ether. The combined organic phases are dried over Na2SO4 and evaporated. The crude product is purified by means of preparative HPLC.

Workup

  1. additionare added under nitrogen atmosphere
  2. additionthe mixture is treated in an ultrasound bath for 10 min
  3. extractionis then extracted three times with ethyl acetate/ether
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. customevaporated
  6. customThe crude product is purified by means of preparative HPLC

Sources & evidence

ORD record
ord-13578d4c243e4abc8f1e0d5c41f7dbd9
Source dataset
uspto-grants-2015_06
Patent number
US09062015B2

Reaction notes

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