Diisopropylethylamine → tert-Butyl 4-((4-nitrobenzo[d]oxazol-2-yl)methyl)piperazine-1-carboxylate

HRID 241803Notes

Reaction equation

HRID 241803 reaction equation
Cl[CH2:2][C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:6]=2[N:7]=1.CCN(C(C)C)C(C)C.[C:24]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>C(#N)C.CCOC(C)=O>[N+:12]([C:8]1[C:6]2[N:7]=[C:3]([CH2:2][N:34]3[CH2:33][CH2:32][N:31]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:36][CH2:35]3)[O:4][C:5]=2[CH:11]=[CH:10][CH:9]=1)([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 99907762-(Chloromethyl)-4-nitro-1,3-benzoxazole

Product 1

HCID 59302730tert-Butyl 4-((4-nitrobenzo[d]oxazol-2-yl)methyl)piperazine-1-carboxylateYield 68%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To room temperature solution of 2-(Chloromethyl)-4-nitrobenzo[d]oxazole (5.15 g, 24.2 mmol, 1.0 equiv) and DIPEA (4.2 mL, 24.2 mmol, 1.0 equiv) in dry acetonitrile (119 mL) was added N-Boc piperazine as a solid in one portion. The reaction was stirred at room temperature overnight. The mixture was diluted with EtOAc (120 mL), washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. Purification on silica gel (20% EtOAc/80% hexanes—100% EtOAc) provided the title compound as a yellow solid (7.0 g, 68%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification on silica gel (20% EtOAc/80% hexanes—100% EtOAc)

Sources & evidence

ORD record
ord-c1dd292989274c2a941d53df62a5e70e
Source dataset
uspto-grants-2014_02
Patent number
US08653081B2

Reaction notes

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