Triethylamine → HCID 54510464, compound

HRID 1108663Notes

Reaction equation

HRID 1108663 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][N:16]=1.C(N(CC)CC)C>>[C:10]([O:9][C:7]([N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH:2]1[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][N:16]=1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 783082-Chloro-5-nitropyridineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 54510464HCID 54510464, compoundYield 101%

Procedure

A mixture of tert-butyl 1-piperazinecarboxylate (1.0 g, 5.3 mmol), 2-chloro-5-nitropyridine (0.85 g, 5.3 mmol) and triethylamine (1.58 mL, 11.0 mmol) in CH3 -CN (50 mL)were stirred at rm temperature for 18 hr. The yellow suspension was concentrated, the residue was taken up in CH2Cl2 (125 mL) and washed with 5% NaHCO3 (2×25 mL) and brine (2×25 mL), dried over MgSO4 and concentrated to dryness in vacuo to yield the yellow titled compound (1.65 g, 100%). MS (ES) m/e 309.2 [m+H]+ 1.

Workup

  1. concentrationThe yellow suspension was concentrated
  2. washwashed with 5% NaHCO3 (2×25 mL) and brine (2×25 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-09d775cd2b274c778388770f320de5ca
Source dataset
uspto-grants-2000_05
Patent number
US06069143

Reaction notes

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