Hydrogen chloride-ethyl acetate → 1-(2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)piperidin-4-ylamine

HRID 39720Notes

Reaction equation

HRID 39720 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][N:12]3[CH2:17][CH2:16][CH:15]([NH:18]C(=O)OC(C)(C)C)[CH2:14][CH2:13]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.Cl.C(OCC)(=O)C>C(OCC)(=O)C>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][N:12]3[CH2:17][CH2:16][CH:15]([NH2:18])[CH2:14][CH2:13]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86669946Tert-butyl (1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-piperidin-4-yl)carbamate

Product 1

HCID 392561291-(2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)piperidin-4-ylamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To 100 mL of an ethyl acetate solution containing 3.62 g of tert-butyl (1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)piperidin-4-yl)carbamate, 30 mL of 4 mol/L hydrogen chloride/ethyl acetate was added, and the mixture was stirred at room temperature for 6 hours. The solvent was removed under reduced pressure, the residue thus obtained was added with ethyl acetate, and a solid substance was collected by filtration. The solid substance thus obtained was purified by silica gel column chromatography [silica gel; Chromatorex-NH, manufactured by Fuji Silysia Chemical Ltd., eluent; chloroform:methanol=5:1] to obtain 1.35 g of a pale yellow oily substance, 1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)piperidin-4-ylamine.

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure
  3. customthe residue thus obtained
  4. filtrationa solid substance was collected by filtration
  5. customThe solid substance thus obtained
  6. customwas purified by silica gel column chromatography [silica gel; Chromatorex-NH, manufactured by Fuji Silysia Chemical Ltd., eluent; chloroform:methanol=5:1]

Sources & evidence

ORD record
ord-cd911618ac7f435690993a9c407ee8bb
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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