Hydrochloric Acid → HCID 57750328, compound

HRID 423111Notes

Reaction equation

HRID 423111 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([NH:14]C(=O)OC(C)(C)C)[CH2:10][CH2:11][O:12][CH3:13])=[CH:5][CH:4]=1>C(Cl)Cl.CO>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([NH2:14])[CH2:10][CH2:11][O:12][CH3:13])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57750355HCID 57750355, compound2×

Product 1

HCID 57750328HCID 57750328, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

Hydrogen chloride (4M in 1,4-dioxane, 0.667 mL, 2.67 mmol) was added to tert-butyl 1-(4-chlorophenyl)-3-methoxypropylcarbamate (Intermediate 99) (80 mg, 0.27 mmol) in a mixture of DCM (5 mL) and methanol (2 mL) at 22° C. The resulting solution was stirred at 22° C. for 5 hours. The mixture was concentrated and the residue was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 2M NH3/MeOH and pure fractions were evaporated to dryness to afford 1-(4-chlorophenyl)-3-methoxypropan-1-amine (47.0 mg, 88%) as a colourless oil.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by ion exchange chromatography
  3. washThe desired product was eluted from the column
  4. customwere evaporated to dryness

Sources & evidence

ORD record
ord-1de4e6293400467786b299d5b3866e52
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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