Hydrochloric Acid → 1-(4-Bromophenyl)cyclopropanamine
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([NH:11]C(=O)OC(C)(C)C)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl>CO.C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([NH2:11])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 35 °C
Procedure
To a solution of tert-butyl [1-(4-bromophenyl)-cyclopropyl]-carbamate (Intermediate 115, 1.08 g, 3.40 mmols) in 20 mL MeOH and 20 mL THF was added 20 mL of 3M aqueous HCl. The solution was warmed to 35° C. for 3 hours and then stirred for 17 h at 25° C. The reaction was quenched by adjusting the pH of the solution to 12 with 3M aqueous NaOH. The mixture was extracted with Et2O and the combined organic layers were washed with H2O and saturated aqueous NaCl before being dried (MgSO4) and concentrated under reduced pressure. The title compound 613 mg (85%) was used without further purification.
Workup
- customThe reaction was quenched
- extractionThe mixture was extracted with Et2O
- washthe combined organic layers were washed with H2O and saturated aqueous NaCl
- dry with materialbefore being dried (MgSO4)
- concentrationconcentrated under reduced pressure
- customThe title compound 613 mg (85%) was used without further purification
Sources & evidence
- ORD record
- ord-6a7460c8466c483ca5a68dec3f8b1f60
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06603019B2
Reaction notes
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