Acetic Acid → HCID 23447435, compound

HRID 2109859Notes

Reaction equation

[C:1]([N:8]1[CH2:13][CH2:12][NH:11][C:10](=[O:14])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:15]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20]Br)#[N:16].[H-].[Na+].C(O)(=O)C>CN(C=O)C>[C:15]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20][N:11]1[CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][C:10]1=[O:14])#[N:16]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 4-Boc-2-piperazinone (2.0 g, 10 mmol), 3-cyanobenzyl bromide (1.8 g, 10 mmol) in DMF (35 mL) at 0° C. was added sodium hydride (480 mg of a 60% suspension in mineral oil, 12 mmol) in several portions over a period of 15 min. The mixture was stirred a 0° C. for 1 h and then at ambient temperature for 1 h. Acetic acid (1 mL) was added and the solvent was removed in vacuo. The residue was partitioned between EtOAc and saturated aqueous sodium bicarbonate solution. The EtOAc layer was separated, dried (MgSO4), filtered, and the solvent was removed in vacuo. The residue was triturated in ether and the white solid was collected by filtration to give 1-(3-cyanobenzyl)4-Boc-2-piperazinone (2.6 g).

Workup

waitat ambient temperature for 1 h
customthe solvent was removed in vacuo
customThe residue was partitioned between EtOAc and saturated aqueous sodium bicarbonate solution
customThe EtOAc layer was separated
dry with materialdried (MgSO4)
filtrationfiltered
customthe solvent was removed in vacuo
customThe residue was triturated in ether
filtrationthe white solid was collected by filtration

Sources & evidence

ORD record: ord-7b863ce5c0ac40cabb4ac8bb5c3948f2
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517532B2

Reaction notes

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