Hydrochloric Acid → 4-(3,4-Dichlorophenoxy)-1-piperidinepropanamine

HRID 1394043Notes

Reaction equation

HRID 1394043 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][NH:15]C(=O)OC(C)(C)C)[CH2:8][CH2:7]1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[O:5][CH:6]1[CH2:7][CH2:8][N:9]([CH2:12][CH2:13][CH2:14][NH2:15])[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11188863Tert-butyl 3-[4-(3,4-dichlorophenoxy)-1-piperidinyl]propylcarbamate

Product 1

HCID 113241264-(3,4-Dichlorophenoxy)-1-piperidinepropanamineYield 73.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The product from Example 2 Step (a) (2 g) was dissolved in dioxan (100 ml) and 6N HCl (100 ml) added. After 18 hrs at room temperature the solvent was evaporated and the resultant solid basified with NaOH (2M) to pH 11. The aqueous was extracted with ethyl acetate, the organic phase separated, dried, filtered and evaporated to leave the sub-title compound as an oil (1.1 g).

Workup

  1. customAfter 18 hrs at room temperature the solvent was evaporated
  2. extractionThe aqueous was extracted with ethyl acetate
  3. customthe organic phase separated
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-a54b165b4cff487da279f19c2d25b56c
Source dataset
uspto-grants-2008_03
Patent number
US07348341B2

Reaction notes

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