Chloroacetyl chloride → Tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate

HRID 923643Notes

Reaction equation

[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:14][CH2:15][C:16](Cl)=[O:17].CCN(C(C)C)C(C)C>>[Cl:14][CH2:15][C:16]([N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1)=[O:17]

Participants

Reactant 3

HCID 6577Chloroacetyl chloride

HCID 81531Diisopropylethylamine

HCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 15829156Tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylateYield 81.1%

Procedure

The above-prepared tert-butyl piperazine-1-carboxylate (500 mg, 2.68 mmol) was treated with chloroacetyl chloride (360 mg, 2.95 mmol) in the presence of DIEA (1.04 g, 8.05 mmol) to give tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate (571 mg, 81% yield) after purification by flash chromatography on a silica gel column (hexane/EtOAc=1:2). C11H19ClN2O3; white solid; mp 68-70° C.; 1H NMR (400 MHz, CDCl3) δ 4.06 (2H, s), 3.58 (2H, m), 3.49 (4H, s), 3.44 (2H, m) 1.47 (9H, s); 13C NMR (100 MHz, CDCl3) δ 164.5, 153.7, 80.2, 46.2, 43.3 (2×), 42.1, 40.9, 28.5; ESI-HRMS calcd for C11H20ClN2O3: 285.0982. found: m/z 285.0985 [M+H]+.

Sources & evidence

ORD record: ord-5861ccc442bf49c8bec57bc74b5a93fe
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278982B2

Reaction notes

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