Triethylamine → tert-Butyl 4-((1,2,4-oxadiazol-3-yl)methyl)piperazine-1-carboxylate

HRID 63590

Reaction equation

HRID 63590 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl[CH2:15][C:16]1[N:20]=[CH:19][O:18][N:17]=1.C(N(CC)CC)C>C(Cl)Cl>[O:18]1[CH:19]=[N:20][C:16]([CH2:15][N:11]2[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH2:12]2)=[N:17]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27357653-(Chloromethyl)-1,2,4-oxadiazole

Product 1

HCID 71481310tert-Butyl 4-((1,2,4-oxadiazol-3-yl)methyl)piperazine-1-carboxylateYield 67.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of Boc-piperazine (571 mg, 3.07 mmol) and 3-(chloromethyl)-1,2,4-oxadiazole (400 mg, 3.37 mmol) in CH2Cl2 (30 mL) was added triethylamine (1.70 mL, 12.3 mmol). The reaction was stirred for 22 h at 50° C. before concentrated in vacuo to give a crude oily white solid. Purification was accomplished by flash chromatography on silica gel (4×12) eluting with MeOH/CH2Cl2 (5%) to yield the title compound (555 mg, 67%) as a white solid. 1H-NMR (500 MHz, CDCl3) 1.43 (s, 9H, C(CH3)3), 2.52 (app t, J=4.9 Hz, 4H, CH2), 3.45 (app t, J=4.9 Hz, 4H, CH2), 3.78 (s, 2H, CH2C—), 8.71 (s, 1H, CHar); LC-MS (ESI, m/z): Rt=1.67 min-213 (M-tBu)+, 169 (M-Boc)+.

Workup

  1. concentrationbefore concentrated in vacuo
  2. customto give a crude oily white solid
  3. customPurification
  4. washeluting with MeOH/CH2Cl2 (5%)

Sources & evidence

ORD record
ord-52229b2901204c4f9b21b8dec07a649b
Source dataset
uspto-grants-2016_09
Patent number
US09447092B2

Linked notes

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