Sodium cyanoborohydride → 6-(4-(4-Nitrophenethyl)-3-oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1466117Notes

Reaction equation

HRID 1466117 reaction equation
O=[C:2]1[CH2:11][CH2:10][C:9]2[CH:8]=[C:7]([C:12]#[N:13])[CH:6]=[CH:5][C:4]=2[CH2:3]1.[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][NH:28][CH2:27][C:26]2=[O:31])=[CH:19][CH:18]=1)([O-:16])=[O:15].C([BH3-])#N.[Na+]>C(O)C.CCOC(C)=O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[N+:14]([C:17]1[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][N:28]([CH:2]3[CH2:11][CH2:10][C:9]4[CH:8]=[C:7]([C:12]#[N:13])[CH:6]=[CH:5][C:4]=4[CH2:3]3)[CH2:27][C:26]2=[O:31])=[CH:21][CH:22]=1)([O-:16])=[O:15]

Participants

7

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 162445046-Oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrileHCID 895248911-[2-(4-Nitrophenyl)ethyl]piperazin-2-one

Product 1

HCID 715256856-(4-(4-Nitrophenethyl)-3-oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-Oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (24 mg, 0.14 mmol) and 1-[2-(4-nitrophenyl)ethyl]piperazin-2-one (20 mg, 0.070 mmol) was treated with titanium(IV) isopropoxide (0.10 ml, 0.35 mmol) for 30 minutes. Then the reaction was diluted with ethanol (5 mL), and sodium cyanoborohydride (44 mg, 0.70 mmol) was added. The reaction was stirred at RT overnight. The reaction was diluted with EtOAc, washed with brine, dried over sodium sulfate, and concentrated to give the crude residue. The desired product was purified by reverse phase HPLC (AcCN-Water with 0.1% TFA). LC-MS (IE, m/z): 405 [M+1]+.

Workup

  1. additionwas added
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ca3a5800606842b7a85fa0f0b6009b19
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

Loading…