Sodium Iodide → 5-[(2-Oxopiperazin-1-yl)methyl]-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

HRID 1466025Notes

Reaction equation

HRID 1466025 reaction equation
ClC[C:3]([N:5]([CH2:16][CH:17]1[C:26]2[C:21](=[C:22]([C:27]#[N:28])[CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][CH2:18]1)[CH2:6][CH2:7][NH:8][C:9](=O)OC(C)(C)C)=[O:4].C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(Cl)Cl>[O:4]=[C:3]1[CH2:9][NH:8][CH2:7][CH2:6][N:5]1[CH2:16][CH:17]1[CH2:18][CH2:19][CH2:20][C:21]2[C:22]([C:27]#[N:28])=[CH:23][CH:24]=[CH:25][C:26]1=2

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 131732672tert-Butyl (2-{(chloroacetyl)[(5-cyano-1,2,3,4-tetrahydronaphthalen-1-yl)methyl]amino}ethyl)carbamate

Product 1

HCID 1175992795-[(2-Oxopiperazin-1-yl)methyl]-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-Butyl (2-{(chloroacetyl)[(5-cyano-1,2,3,4-tetrahydronaphthalen-1-yl)methyl]amino}ethyl)carbamate (120 mg, 0.29 mmol) in DCM (5 mL) was added TFA (0.5 mL) and stirred at ambient temperature for 2 h until TLC indicated the starting material was consumed completely. The solvent was evaporated in vacuum. The residue was dissolved in ethanol (10 mL) and K2CO3 (120 mg, 0.9 mmol) and catalytic NaI was added. The reaction mixture was refluxed overnight, then the salt was removed by filtration. The filtrate was evaporated under vacuum, and then water (10 mL) and DCM (10 mL) was added. The mixture was extracted with DCM (10 mL×3), dried over anhydrous Na2SO4, and evaporated to give the title compound. 1H-NMR (400 MHz, CDCl3) δ ppm 7.42 (d, J=7.6 Hz, 1H), 7.33 (d, J=7.6 Hz, 1H), 7.15 (t, J=7.6 Hz, 1H), 3.66-3.72 (m, 1H), 3.54 (s, 2H), 3.21-3.32 (m, 4H), 2.98-3.11 (m, 3H), 2.75-2.85 (m, 1H), 1.78-1.94 (m, 2H), 1.71-1.75 (m, 2H).

Workup

  1. customwas consumed completely
  2. customThe solvent was evaporated in vacuum
  3. dissolutionThe residue was dissolved in ethanol (10 mL)
  4. temperatureThe reaction mixture was refluxed overnight
  5. customthe salt was removed by filtration
  6. customThe filtrate was evaporated under vacuum
  7. additionwater (10 mL) and DCM (10 mL) was added
  8. extractionThe mixture was extracted with DCM (10 mL×3)
  9. dry with materialdried over anhydrous Na2SO4
  10. customevaporated

Sources & evidence

ORD record
ord-8f74269ff0ac46169c63ca9b8fcda8c5
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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