3,4-Dichlorobenzyl chloride → 1-[(3,4-Dichlorophenyl)methyl]piperidin-4-amine

HRID 1072487Notes

Reaction equation

HRID 1072487 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][C:3]=1[Cl:10].[NH:11]1[CH2:16][CH2:15][CH:14]([NH:17]C(=O)OC(C)(C)C)[CH2:13][CH2:12]1>CN(C=O)C.C(N(CC)CC)C>[Cl:10][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:2]=1[Cl:1])[CH2:8][N:11]1[CH2:16][CH2:15][CH:14]([NH2:17])[CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 76093,4-Dichlorobenzyl chlorideHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 109781561-[(3,4-Dichlorophenyl)methyl]piperidin-4-amineYield 58.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

1,2-dichloro-4-(chloromethyl)benzene (390 mg, 1.99 mmol)) was added to a solution of tert-butyl 4-piperidinylcarbamate (400 mg, 2.0 mmol) in DMF (25 ml) and triethylamine (2 ml). The solution was stirred at room temperature for 3 hrs and then concentrated in vacuo. To the solution of the solid in dichloromethane was added (30 ml) trifluoroacetic acid (6 ml) was added and stirred at room temperature for 2 hrs. The solution was diluted with dichloromethane and washed with two portions of water. The combined water washings were treated with 2M NaOH to pH 10 and extracted with ether. The ether was dried (Na2SO4), filtered and evaporated to leave a yellow residue (300 mg, 1.16 mmol).

Workup

  1. concentrationconcentrated in vacuo
  2. additionTo the solution of the solid in dichloromethane was added (30 ml) trifluoroacetic acid (6 ml)
  3. additionwas added
  4. stirringstirred at room temperature for 2 hrs
  5. additionThe solution was diluted with dichloromethane
  6. washwashed with two portions of water
  7. additionThe combined water washings were treated with 2M NaOH to pH 10
  8. extractionextracted with ether
  9. dry with materialThe ether was dried (Na2SO4)
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-af5ec65301374a29b8c10494afd35268
Source dataset
uspto-grants-2005_06
Patent number
US06911458B2

Reaction notes

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