Triethylamine → Benzyl 4-(cyclopropylcarbonyl)piperazine-1-carboxylate

HRID 1436976Notes

Reaction equation

HRID 1436976 reaction equation
[N:1]1([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH:17]1([C:20](O)=[O:21])[CH2:19][CH2:18]1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.O>[CH:17]1([C:20]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:8])[CH2:2][CH2:3]2)=[O:21])[CH2:19][CH2:18]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 15655Cyclopropanecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 643495Benzyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 23069850Benzyl 4-(cyclopropylcarbonyl)piperazine-1-carboxylateYield 93.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In 35 mL of N,N-dimethylformamide were dissolved benzyl 1-piperazinecarboxylate (5.00 g, 22.7 mmol) and cyclopropanecarboxylic acid (2.54 g, 29.5 mmol), and 1-ethyl-3-(3-(N,N-dimethylamino)propyl)-carbodiimide hydrochloride (6.53 g, 34.1 mmol), 1-hydroxybenzotriazole (4.52 g, 29.5 mmol) and triethylamine (3.60 g, 35.9 mmol) were added thereto at room temperature, followed by stirring at the same temperature for three hours. The reaction mixture was mixed with water, and extracted twice with ethyl acetate. The organic layer was sequentially washed with water twice, with a saturated aqueous solution of sodium bicarbonate once and with brine once, and then dried over anhydrous sodium sulfate. The organic layer was passed through a silica gel column (Fuji Silysia, NH Silica gel) and evaporated to give the title compound (6.10 g, 93.1%) as a white amorphous.

Workup

  1. additionwere added
  2. customat room temperature
  3. extractionextracted twice with ethyl acetate
  4. washThe organic layer was sequentially washed with water twice
  5. dry with materialwith a saturated aqueous solution of sodium bicarbonate once and with brine once, and then dried over anhydrous sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-86ef89a4dde243d895e6fceefa5a7d48
Source dataset
uspto-grants-2009_11
Patent number
US07619100B2

Reaction notes

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