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Hydrochloric Acid → 1-(4-Bromophenyl)cyclopropanamine

HRID 24204
Notes
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Reaction equation

HRID 24204 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]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53216208tert-Butyl (1-(4-bromophenyl)cyclopropyl)carbamate2×

Product 1

HCID 187101951-(4-Bromophenyl)cyclopropanamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

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

  1. customThe reaction was quenched
  2. extractionThe mixture was extracted with Et2O
  3. washthe combined organic layers were washed with H2O and saturated aqueous NaCl
  4. dry with materialbefore being dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe title compound 613 mg (85%) was used without further purification

Sources & evidence

ORD record
ord-45d832dfa241442bbc83a81f36563672
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06855512B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes