4-(Trifluoromethoxy)benzenemethanol → HCID 69141711, compound

HRID 1794062Notes

Reaction equation

HRID 1794062 reaction equation
CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][N:29]([C:32](Cl)=[O:33])[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].[F:35][C:36]([F:47])([F:46])[O:37][C:38]1[CH:45]=[CH:44][C:41]([CH2:42][OH:43])=[CH:40][CH:39]=1>C(#N)C>[F:35][C:36]([F:46])([F:47])[O:37][C:38]1[CH:45]=[CH:44][C:41]([CH2:42][O:43][C:32]([N:29]2[CH2:30][CH2:31][N:26]([C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:25])[CH2:27][CH2:28]2)=[O:33])=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 1371844-(Trifluoromethoxy)benzenemethanolHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 11334154Tert-butyl 4-(chlorocarbonyl)piperazine-1-carboxylate

Product 1

HCID 69141711HCID 69141711, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

652 mg (1.5 mmol) PS-BEMP and 373 mg (1.5 mmol) 4-chlorocarbonyl-piperazine-1-carboxylic acid tert-butyl ester was added to a solution of 192 mg (1.0 mmol) 4-trifluoromethoxybenzyl alcohol in 5 ml acetonitrile. The mixture was heated to reflux for 24 h then cooled to rt, diluted with 5 ml acetonitrile, 666 mg (4.5 mmol) PS-NH2 added and shaken at rt for 16 h. After filtration and evaporation the crude product is purified by flash chromatography on silica gel with hexane/AcOEt 50:50: 180 mg colourless crystalline solid. 1H-NMR (CDCl3): 1.45 s, 9H, 3.35–3.55 m, 8H, 5.14 s, 2H, 7.20 d, 2H and 7.40 d, 2H, AB-system.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 24 h
  3. additionadded
  4. filtrationAfter filtration and evaporation the crude product
  5. customis purified by flash chromatography on silica gel with hexane/AcOEt 50:50

Sources & evidence

ORD record
ord-e99f606e8e264e1a87617001d9106f85
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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