Ethanol → HCID 117599397, compound

HRID 1466123Notes

Reaction equation

HRID 1466123 reaction equation
Cl.[CH3:2][CH:3]1[NH:8][CH2:7][CH2:6][N:5]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[C:4]1=[O:20].[N+:21]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH:31]=O)=[CH:26][CH:25]=1)([O-:23])=[O:22].C(O)C.C([BH3-])#N.[Na+]>C(OCC)(=O)C>[CH3:2][CH:3]1[N:8]([CH2:31][CH2:30][C:27]2[CH:26]=[CH:25][C:24]([N+:21]([O-:23])=[O:22])=[CH:29][CH:28]=2)[CH2:7][CH2:6][N:5]([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)[C:4]1=[O:20]

Participants

6

Reactant 4

HCID 702EthanolHCID 5003444Sodium cyanoborohydrideHCID 11744988(4-Nitrophenyl)acetaldehydeHCID 89525148HCID 89525148, compound

Product 1

HCID 117599397HCID 117599397, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 3-Methyl-1-[2-(4-nitrophenyl)ethyl]piperazin-2-one hydrochloride (38 mg, 0.13 mmol) and (4-Nitrophenyl)acetaldehyde (31 mg, 0.19 mmol) was added_titanium(IV) isopropoxide (0.37 mL, 1.3 mmol). After stirring the mixture at RT for 15 minutes, ethanol (2 mL) and sodium cyanoborohydride (80 mg, 1.3 mmol) were added to the reaction. The mixture was allowed to stir at RT for 16 hours. The reaction was diluted with ethyl acetate, washed with brine, dried over sodium sulfate, and concentrated to give the crude title product. The title product was purified by mass-directed reverse phase HPLC (AcCN-Water with 0.1% TFA). LC-MS (IE, m/z): 413 [M+1]+.

Workup

  1. stirringto stir at RT for 16 hours
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-50a611d60d1c4c25acc76c665083b91e
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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