Tert-Butylamine → Tert-butyl({[2-(4-methylpiperazin-1-yl)-5-nitrophenyl]methyl})amine

HRID 1190867Notes

Reaction equation

HRID 1190867 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=2[CH2:17]O)[CH2:4][CH2:3]1.S(Cl)(Cl)=O.[C:23]([NH2:27])([CH3:26])([CH3:25])[CH3:24]>C1COCC1>[C:23]([NH:27][CH2:17][C:9]1[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:8]=1[N:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1)([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 24386Thionyl ChlorideHCID 25918812[2-(4-Methylpiperazino)-5-nitrophenyl]methanol

Product 1

HCID 67247988Tert-butyl({[2-(4-methylpiperazin-1-yl)-5-nitrophenyl]methyl})amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To [2-(4-methylpiperazin-1-yl)-5-nitrophenyl]methanol prepared in step A of example 1 (0.150 g, 0.60 mmol) in 5 mL of THF at 0° C. was added thionyl chloride (0.22 mL, 5 eq). The reaction mixture was refluxed for 45 minutes and then the solvent and the excess of thionyl chloride were evaporated. The residue was suspended in 5 mL of acetonitrile and tert-butylamine (0.62 mL, 10 eq) was added at 0° C. The solution was stirred 48 h at room temperature, evaporated and the residue was dissolved in ethyl acetate and washed with a saturated aqueous solution of Na2CO3. The aqueous layer was extracted with ethyl acetate and then the combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was thoroughly washed with pentane and filtered off to yield expected compound as an orange powder (0.192 g, quantitative yield) m/z (ESI) 307.2 [M+H]+.

Workup

  1. temperatureThe reaction mixture was refluxed for 45 minutes
  2. customthe solvent and the excess of thionyl chloride were evaporated
  3. customevaporated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with a saturated aqueous solution of Na2CO3
  6. extractionThe aqueous layer was extracted with ethyl acetate
  7. dry with materialthe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. washThe residue was thoroughly washed with pentane
  11. filtrationfiltered off

Sources & evidence

ORD record
ord-7b958d57f5874352b7a362208f5f190a
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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