Trifluoroacetic acid → N-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-methylpiperidine-4-amine

HRID 39675Notes

Reaction equation

HRID 39675 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][NH:12][C:13]3([CH3:26])[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][NH:12][C:13]3([CH3:26])[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59398035Tert-butyl 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-4-methylpiperidine-1-carboxylate

Product 1

HCID 59398095N-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-methylpiperidine-4-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5 mL of a dichloromethane solution containing 0.66 g of tert-butyl 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-4-methylpiperidine-1-carboxylate, 5 mL of trifluoroacetic acid was added, and the mixture was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure, and thereto were added chloroform, water and 6 mol/L hydrochloric acid. The aqueous layer was separated, and the aqueous layer was washed with chloroform. Chloroform was added to the aqueous layer, and the resultant solution was adjusted to pH 13 with a 20% aqueous sodium hydroxide solution. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 0.26 g of a colorless oily substance, N-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-methylpiperidine-4-amine.

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure
  3. additionwere added chloroform, water and 6 mol/L hydrochloric acid
  4. customThe aqueous layer was separated
  5. washthe aqueous layer was washed with chloroform
  6. additionChloroform was added to the aqueous layer
  7. customThe organic layer was separated
  8. extractionthe aqueous layer was extracted with chloroform
  9. dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
  10. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0282007060ac43959ea3bfbb5904e86e
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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