Hydrochloric Acid → N-(4-((trans)-2-aminocyclopropyl)phenyl)acetamide, hydrochloride

HRID 529335Notes

Reaction equation

HRID 529335 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]2[CH2:13][C@H:12]2[NH:14]C(=O)OC(C)(C)C)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[ClH:22]>O1CCOCC1>[ClH:22].[NH2:14][C@@H:12]1[CH2:13][C@H:11]1[C:8]1[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86708244Tert-butyl ((trans)-2-(4-acetamidophenyl)cyclopropyl)carbamate

Product 1

HCID 131731922N-(4-((trans)-2-aminocyclopropyl)phenyl)acetamide, hydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To tert-butyl ((trans)-2-(4-acetamidophenyl)cyclopropyl)carbamate, step 1 (900 mg, 3.10 mmol) was added 4M HCl (3.444 mL, 13.78 mmol) in 1,4-dioxane and stirred for 2 h at RT. The reaction mixture was concentrated and triturated with EtOAc (10 mL) and dried under vacuum to afford N-(4-((trans)-2-aminocyclopropyl)phenyl)acetamide, hydrochloride (700 mg, 99% yield) as off white solid. LCMS (ES) m/e 190.2 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customtriturated with EtOAc (10 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-267cd33a52664c6cbd1de981260e429f
Source dataset
uspto-grants-2016_05
Patent number
US09346840B2

Reaction notes

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