1,2-Dichloroethane → Ethyl acetate hexane

HRID 1592737Notes

Reaction equation

HRID 1592737 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][NH2:21])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])(C)C)=[O:2].[C:22](O)(=[O:25])[CH2:23][CH3:24].[CH:27]1[CH:28]=[CH:29][C:30]2N(O)N=N[C:31]=2[CH:32]=1.[CH2:37](Cl)CCl.CCN(C(C)C)C(C)C>C1COCC1>[C:22]([NH:21][CH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)(=[O:25])[CH2:23][CH3:24].[CH3:29][CH2:28][CH2:27][CH2:32][CH2:31][CH3:30].[C:1]([O:3][CH2:4][CH3:7])(=[O:2])[CH3:37]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 1032Propionic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 4961274Tert-butyl 4-[2-(aminomethyl)phenyl]piperazine-1-carboxylate

Product 2

HCID 21226206Ethyl acetate hexaneYield 167.5%HCID 58996649HCID 58996649, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Alternatively, the title compound was prepared in the following procedure: About 0.40 g (1.37 mmol) of 1-Boc-4-(2-aminomethyl-phenyl)-piperazine, 0.11 ml of (1.51 mmol) propionic acid, 0.22 g (1.64 mmol) of HOBt, 0.31 g (1.64 mmol) of EDC, and 0.24 ml (1.37 mmol) of DIEA were mixed in 30 ml THF under nitrogen and stirred overnight at r.t. The reaction was concentrated to dryness and ethyl acetate was added. The mixture was washed with saturated bicarbonate and brine, and then dried with sodium sulfate. The residue was purified by flash chromatography eluting with 1:1 hexane/ethyl acetate giving about 0.4 g (86% yield). The material was deprotected using TFA/DCM to give 4-[2-(propionylamino-methyl)-phenyl]-piperazine. LRMS (ESI+): 248 (M+1)

Workup

  1. concentrationThe reaction was concentrated to dryness and ethyl acetate
  2. additionwas added
  3. washThe mixture was washed with saturated bicarbonate and brine
  4. dry with materialdried with sodium sulfate
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-06c7d5470db84df5bf8eee80117b3ecc
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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