Succinic anhydride → 1-(t-Butyloxycarbonyl)-4-(2-(4-hydroxy-4-oxo-butanoyloxy)ethyl)piperazine

HRID 1950744Notes

Reaction equation

HRID 1950744 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.[C:17]1(=[O:23])[O:22][C:20](=[O:21])[CH2:19][CH2:18]1>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[C:13]([O:12][C:10]([N:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][O:1][C:17](=[O:23])[CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH2:5][CH2:6]1)=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 7922Succinic anhydrideHCID 735736Tert-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylate

Product 1

HCID 584825771-(t-Butyloxycarbonyl)-4-(2-(4-hydroxy-4-oxo-butanoyloxy)ethyl)piperazine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

Compound 57 (5.3 g, 23.0 mmol), succinic anhydride (2.30 g, 23.0 mmol) and 4-dimethylaminopyridine (281 mg, 2.30 mmol) were dissolved in CHCl3 (14 mL) and stirred for 18 h. The solution was concentrated in vacuo and used without further purification. 1H NMR (400 MHz, CDCl3) δ 1.42 (s, 9H), 2.54-2.60 (m, 8H), 2.72 (t, J=5.6, 2H), 3.43-3.46 (m, 4H), 4.23 (t, J=5.5, 2H).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customused without further purification

Sources & evidence

ORD record
ord-d77c103601de4ddf90359c282e5ccddf
Source dataset
uspto-grants-2013_03
Patent number
US08404664B2

Reaction notes

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