Hydrochloric Acid → Tert-butyl 4-(2,2,2-trifluoroacetyl)piperazine-1-carboxylate

HRID 1961368Notes

Reaction equation

HRID 1961368 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[O:20](C(C(F)(F)F)=O)[C:21]([C:23]([F:26])([F:25])[F:24])=O.Cl>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:21](=[O:20])[C:23]([F:26])([F:25])[F:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 20294522Tert-butyl 4-(2,2,2-trifluoroacetyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of piperazine-1-carboxylic acid tert-butyl ester (10 g, 53.69 mmol) and pyridine (8.7 mL, 107.57 mmol) in CH2Cl2 (100 mL) was added dropwise (CF3CO)2O (10.5 mL, 75.54 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 2 h. 2N HCl (60 mL) was then added. The organic layer was dried over MgSO4, filtered, and then concentrated. The resulting residue, the title compound, was used in the next reaction without further purification. MS m/z (MH+-Boc) 183.1, (MH+—C4H9) 227.1; 1H NMR (300 MHz, CDCl3): δ 3.45-3.7 (m, 8H), 1.5 (s, 9H).

Workup

  1. dry with materialThe organic layer was dried over MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe resulting residue, the title compound, was used in the next reaction without further purification

Sources & evidence

ORD record
ord-25c2b0657d5d4e2ab8be1e7d0592a437
Source dataset
uspto-grants-2013_04
Patent number
US08415341B2

Reaction notes

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