Triphenylphosphine → 4-[2-(2-Morpholin-4-yl-ethoxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 456439

Reaction equation

HRID 456439 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[OH:34])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].[N:35]1([CH2:41][CH2:42]O)[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:15]([O:19][C:20]([N:22]1[CH2:23][CH2:24][N:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][CH2:42][CH2:41][N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)[CH2:26][CH2:27]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 11543684Tert-butyl 4-(2-hydroxyphenyl)piperazine-1-carboxylate

Product 1

HCID 184367644-[2-(2-Morpholin-4-yl-ethoxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl esterYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Diisopropyl azodicarboxylate (0.48 mL, 2.4 mmol) was added dropwise to a stirred solution of 4-(2-hydroxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (0.56 g, 2 mmol), 2-morpholin-4-yl-ethanol (0.24 mL, 2 mmol) and triphenylphosphine (0.63 g, 2.4 mmol) in THF (20 mL) cooled to 0° C. The resulting solution was warmed to r.t. and stirred for about 16 hours. The solvent was removed in vacuo and the residue purified by silica gel chromatography (ethyl acetate) to afford the final compound (0.50 g, 64%) as a clear oil

Workup

  1. temperatureThe resulting solution was warmed to r.t.
  2. customThe solvent was removed in vacuo
  3. customthe residue purified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-a1e654ad91ad4cd192c716c8c40a3aaa
Source dataset
uspto-grants-2007_03
Patent number
US07186715B2

Linked notes

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