Triethylamine → HCID 22418714, compound

HRID 982530Notes

Reaction equation

HRID 982530 reaction equation
[N+]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:5]=1)([O-])=O.[CH2:16]([N:18](CC)[CH2:19][CH3:20])[CH3:17].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>C(Cl)Cl.CCOCC>[CH2:16]([N:18]([CH2:19][CH3:20])[C:9]1[CH:4]=[CH:5][C:6]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:7][CH:8]=1)[CH3:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 224187101-(4-Nitro-2-pyridinyl)piperazine

Product 1

HCID 22418714HCID 22418714, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

The amine (21 g), triethylamine (17.9 g) and methylene chloride (600 ml) are cooled to 0°. Di-t-butyl dicarbonate (25.8 g) in methylene chloride (200 ml) is added over 30 min at 0°. The reaction mixture is stirred at 0° for 1 hr and allowed to warm to 20-25°. The reaction mixture is washed with saturated sodium bicarbonate (3×200 ml), dried over potassium carbonate and the solvent removed under reduced pressure to give a solid. The solid is dissolved in ether, petroleum ether is added until the mixture is cloudy, the mixture is filtered thru celite and the filtrate is concentrated to give the protected piperazine compound.

Workup

  1. temperatureto warm to 20-25°
  2. washThe reaction mixture is washed with saturated sodium bicarbonate (3×200 ml)
  3. dry with materialdried over potassium carbonate
  4. customthe solvent removed under reduced pressure
  5. customto give a solid
  6. filtrationthe mixture is filtered thru celite
  7. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-2e5e1074cb194e1198967d50109f4977
Source dataset
uspto-grants-1991_02
Patent number
US04996318

Reaction notes

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