Hydrochloric Acid → 1-(4-Bromophenyl)cyclopropanamine

HRID 841697Notes

Reaction equation

C(OC(=O)[NH:7][C:8]1([C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=2)[CH2:10][CH2:9]1)(C)(C)C.Cl>CO.C1COCC1>[Br:17][C:14]1[CH:13]=[CH:12][C:11]([C:8]2([NH2:7])[CH2:9][CH2:10]2)=[CH:16][CH:15]=1

Participants

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 17h 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-41cb7613b07049b3b126efb1a408e5a9
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06369261B1

Reaction notes

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