Tributylphosphine → HCID 67328618, compound

HRID 1023329Notes

Reaction equation

HRID 1023329 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:23]=[CH:22][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:6][CH:5]=1.O[C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][N:26]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1>[CH3:31][C:28]1[CH:29]=[CH:30][C:25]([O:1][CH2:2][CH2:3][C:4]2[CH:5]=[CH:6][C:7]([CH2:8][N:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[CH2:11][CH2:10]3)=[CH:22][CH:23]=2)=[N:26][CH:27]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 67328866Tert-butyl 4-[4-(2-hydroxyethyl)benzyl]piperazine-1-carboxylateHCID 178426911HCID 178426911, compound

Product 1

HCID 67328618HCID 67328618, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

tert-Butyl 4-[4-(2-hydroxyethyl)benzyl]piperazine-1-carboxylate (1.44 g), 2-hydroxy-5-methylpyridine (0.737 g), tri-n-butylphosphine (1.76 mL), 1,1′-(azodicarbonyl)-dipiperidine (1.70 g), and THF (16.5 mL) were mixed in a 20 mL process vial. The vial was sealed, and the reaction mixture was heated with microwaves to 55 ° C. for 10 minutes. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt =10/1 to 3/10) to give tert-butyl 4-(4-{2-[(5-methylpyridin-2-yl)oxy]ethyl}benzyl)piperazine-1-carboxylate as a pale yellow amorphous (1.01 g).

Workup

  1. customThe vial was sealed
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt =10/1 to 3/10)

Sources & evidence

ORD record
ord-efe7faaf3c27451abaac08b2f664dabc
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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