Triethylamine → Benzyl 4-(2-aminoethyl)piperazine-1-carboxylate

HRID 420852Notes

Reaction equation

HRID 420852 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.C(N(CC)CC)C.Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:6][CH2:5]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8795AminoethylpiperazineHCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 10890711Benzyl 4-(2-aminoethyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

N-(2-Aminoethyl)piperazine (4.93 g) was dissolved in tetrahydrofuran (40 ml), and the solution was added with triethylamine (10.6 ml). The mixture was added with a solution of benzyl chloroformate (4.9 ml) in tetrahydrofuran (40 ml) under ice cooling, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with ethyl acetate and saturated aqueous sodium hydrogencarbonate, the layers were separated, and then the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia=10:1:0.1) to obtain the title compound (400 mg).

Workup

  1. customthe layers were separated
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia=10:1:0.1)

Sources & evidence

ORD record
ord-bdfe9dff823441fb8f66da1da7645455
Source dataset
uspto-grants-2012_01
Patent number
US08097708B2

Reaction notes

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