Hydrochloric Acid → 2-(4-Chlorophenyl)cyclopropan-1-amine hydrochloride

HRID 1021434Notes

Reaction equation

HRID 1021434 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][CH:9]2[NH:11]C(=O)OC(C)(C)C)=[CH:4][CH:3]=1.Cl.O1CCOCC1>ClCCl>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:10][CH:9]2[NH2:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67080543Tert-butyl 2-(4-chlorophenyl)cyclopropylcarbamate

Product 1

HCID 462211102-(4-Chlorophenyl)cyclopropan-1-amine hydrochlorideYield 198.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 2-(4-chlorophenyl)cyclopropylcarbamate (51.9 mg, 0.1938 mmol) was dissolved in Dichloromethane (1 ml) and 4M HCl solution in dioxane (0.4846 ml, 1.938 mmol) was added. The mixture was stirred for 3 hours at ambient temperature, during which time a white solid precipitated out of solution. The crude mixture was concentrated and chased with EtOAc (2×10 ml). The residual fine solid was dried under high vacuum to provide 39.2 mg of the title compound as a solid (99%).

Workup

  1. customprecipitated out of solution
  2. concentrationThe crude mixture was concentrated
  3. customThe residual fine solid was dried under high vacuum

Sources & evidence

ORD record
ord-032c296d98a94786b938de3b4ed9546c
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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