Triethylamine → HCID 67972673, compound

HRID 1804636Notes

Reaction equation

HRID 1804636 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[O:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1.[CH3:25]CN(CC)CC>C1COCC1>[O:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=[C:16]1[CH2:15][N:11]1[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH:12]1[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 20619892-(Chloromethyl)-1,3-benzoxazole

Product 1

HCID 67972673HCID 67972673, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of N—BOC-piperazine (2.22 g, 11.93 mmol) and 2-chloromethylbenzoxazole (2 g, 11.93 mmol) in anhydrous THF (20 ml) was added Et3N (2.5 ml, 17.9 mmol) and the resulting mixture stirred at RT overnight. Partitioned between water and EtOAc, organic layer washed with sat. NaCl, dried over MgSO4, filtered and evaporated. The residue purified by MPLC (Biotage Horizon: FLASH 40+M) eluent: 100% Hexanes (190 ml), gradient rising from 100% Hexanes to 50% EtOAc in Hexanes (900 ml), then 50% EtOAc in Hexanes (500 ml) to give 2.63 g (69%) of the title compound as a light pink solid. 1H NMR (CDCl3): 1.45 (s, 9H), 2.58 (m, 4H), 3.49 (m, 4H), 3.89 (s, 2H), 7.33 (m, 2H), 7.53 (m, 1H), 7.71 (m, 1H).

Workup

  1. customPartitioned between water and EtOAc, organic layer
  2. washwashed with sat. NaCl
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue purified by MPLC (Biotage Horizon: FLASH 40+M) eluent

Sources & evidence

ORD record
ord-d639fca9e7ac42db8d4229110457a6c1
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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