Hydrochloric Acid → 1-(Trifluoromethyl)cyclopropanamine hydrochloride

Reaction equation

[F:1][C:2]([F:15])([F:14])[C:3]1([NH:6]C(=O)OC(C)(C)C)[CH2:5][CH2:4]1.[ClH:16]>>[ClH:16].[F:1][C:2]([F:15])([F:14])[C:3]1([NH2:6])[CH2:5][CH2:4]1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 11658639Tert-butyl [1-(trifluoromethyl)cyclopropyl]carbamate

Product 1

HCID 116511961-(Trifluoromethyl)cyclopropanamine hydrochlorideYield 91%

Procedure

Tert-butyl 1-(trifluoromethyl)cyclopropylcarbamate (4.08 g, 18.3 mmol) was suspended in 1 N HCl(aq) (150 mL) and stirred at reflux for 3.5 h. The solution was concentrated in vacuo and the residue was triturated with acetone. The filtrate was collected, concentrated, and the residue triturated with diethyl ether to afford 2.67 g (91%) of 1-(trifluoromethyl)cyclopropylamine hydrochloride as a white solid.

Workup

temperatureat reflux for 3.5 h
concentrationThe solution was concentrated in vacuo
customthe residue was triturated with acetone
customThe filtrate was collected
concentrationconcentrated
customthe residue triturated with diethyl ether

Sources & evidence

ORD record: ord-156c063e1b044551b05abc469f8230ec
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536187B2

Reaction notes

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