Sodium Bicarbonate → 1-(Chloroacetyl)-4-cyclobutylpiperazine

HRID 1713076Notes

Reaction equation

HRID 1713076 reaction equation
C(=O)(O)[O-].[Na+].[Cl:6][CH2:7][C:8](Br)=[O:9].[CH:11]1([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH2:14][CH2:13][CH2:12]1>O.C(Cl)Cl>[Cl:6][CH2:7][C:8]([N:18]1[CH2:19][CH2:20][N:15]([CH:11]2[CH2:14][CH2:13][CH2:12]2)[CH2:16][CH2:17]1)=[O:9]

Participants

6

Reactant 3

HCID 516892Sodium Bicarbonate2×HCID 47386021-CyclobutylpiperazineHCID 12610899Chloroacetyl bromide

Product 1

HCID 574205621-(Chloroacetyl)-4-cyclobutylpiperazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of sodium bicarbonate (15 mmol) in water (5 mL) and DCM (30 mL) at 0° C. is added chloroacetyl bromide (12 mmol), followed by immediate addition of 1-cyclobutylpiperazine (10 mmol). The mixture is stirred at 0° C. for an additional 40 min. To the mixture is added aqueous sodium bicarbonate (15 mL) and DCM (30 mL). The layers are separated and the organic layer is dried (MgSO4) and solvent is removed in vacuo to give 2-chloro-1-(4-cyclobutyl-piperazin-1-yl)-ethanone, which is used in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 4.07 (2H, s), 3.64 (2H, t), 3.52 (2H, t), 2.74 (1H, m), 2.36 (2H, t), 2.31 (2H, t), 1.72-2.08 (6H, m); MS (+VE) m/z 217.1 (M++1).

Workup

  1. customThe layers are separated
  2. dry with materialthe organic layer is dried (MgSO4) and solvent
  3. customis removed in vacuo

Sources & evidence

ORD record
ord-8e4abdf4a7e44e8998d6a9f474db4b00
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

Loading…