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Ethanol → 4-(2-{4-[2-(4-Nitrophenyl)ethyl]-3-oxopiperazin-1-yl}ethyl)benzonitrile

HRID 1466122
Notes
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Reaction equation

HRID 1466122 reaction equation
O=[CH:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1.[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][NH:26][CH2:25][C:24]2=[O:29])=[CH:17][CH:16]=1)([O-:14])=[O:13].C(O)C.C([BH3-])#N.[Na+]>C(OCC)(=O)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][N:26]([CH2:2][CH2:3][C:4]3[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=3)[CH2:25][C:24]2=[O:29])=[CH:17][CH:16]=1)([O-:14])=[O:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 702EthanolHCID 5003444Sodium cyanoborohydrideHCID 125916704-(2-Oxoethyl)benzonitrileHCID 895248911-[2-(4-Nitrophenyl)ethyl]piperazin-2-one

Product 1

HCID 895334784-(2-{4-[2-(4-Nitrophenyl)ethyl]-3-oxopiperazin-1-yl}ethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 11026
Titanium isopropoxide
Catalyst
HCID 8857Ethyl AcetateSolvent

Procedure

The crude 4-(2-Oxoethyl)benzonitrile (100 mg, 0.69 mmol) was treated with 1-[2-(4-nitrophenyl)ethyl]piperazin-2-one (197 mg, 0.69 mmol) and titanium(IV) isopropoxide (2.0 mL). After stirring the mixture for 15 minutes, ethanol and sodium cyanoborohydride was added into the reaction. The mixture was allowed to stir for 4 hours. The reaction was diluted with ethyl acetate, washed with brine, dried over sodium sulfate, and concentrated to give the crude residue. The desired product was purified by mass-directed reverse phase HPLC (AcCN-Water with 0.1% TFA). LC-MS (IE, m/z): 378 [M+1]+.

Workup

  1. stirringto stir for 4 hours
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1177e41e43bb4b40a8f497095486df29
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08999990B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes