Hydrochloric Acid → HCID 11557554, compound

HRID 423052Notes

Reaction equation

HRID 423052 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([NH:15]C(=O)OC(C)(C)C)[CH2:10][CH2:11][N:12]([CH3:14])[CH3:13])=[CH:5][CH:4]=1>C(Cl)Cl.CO>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([NH2:15])[CH2:10][CH2:11][N:12]([CH3:14])[CH3:13])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57750395HCID 57750395, compound2×

Product 1

HCID 11557554HCID 11557554, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

Hydrogen chloride (4M in dioxane, 1.132 mL, 32.61 mmol) was added to tert-butyl 1-(4-chlorophenyl)-3-(dimethylamino)propylcarbamate (Intermediate 32) (0.051 g, 0.16 mmol) in a mixture of DCM (5 mL) and methanol (2 mL) at 22° C. The resulting solution was stirred at 22° C. for 4 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)-N3,N3-dimethylpropane-1,3-diamine (0.032 g, 92%) 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-3ecd8b09d8204254af985f87f24b941d
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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