Dichloromethane → cis-2-(4-Fluoro-phenyl)-cyclopropylamine hydrochloride

HRID 1479151Notes

Reaction equation

HRID 1479151 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:10][C@@H:9]1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)(C)(C)C.CCOC(C)=O.C1CCCCC1.[Cl:31]CCl>>[ClH:31].[F:17][C:14]1[CH:13]=[CH:12][C:11]([C@H:9]2[CH2:10][C@H:8]2[NH2:7])=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 21867204Cyclohexane ethylacetateHCID 89760766Cis-2-(4-Fluoro-Phenyl)-Cyclopropyl-Carbamic Acid Tert-Butyl Ester

Product 1

HCID 89760855cis-2-(4-Fluoro-phenyl)-cyclopropylamine hydrochlorideYield 87%

Procedure

cis-2-(4-Fluoro-phenyl)-cyclopropyl-carbamic acid tert-butyl ester (0.239 g, 0.951 mmol) was dissolved in dichloromethane (5 ml). Under argon HCl (4 M in dioxan, 2.38 ml, 9.5 mmol) was added and the clear solution stirred at room temperature. After 3 hours a precipitate had formed and the reaction was complete according to tlc (30% EtOAc/cyclohexane) and LC/MS. The solvent was evaporated and the residue stirred with tBuOMe. The solid was filtered off and washed twice with tBuOMe and dried to yield 155 mg (87%) of the product as a white solid.

Workup

  1. additionUnder argon HCl (4 M in dioxan, 2.38 ml, 9.5 mmol) was added
  2. customAfter 3 hours a precipitate had formed
  3. customThe solvent was evaporated
  4. stirringthe residue stirred with tBuOMe
  5. filtrationThe solid was filtered off
  6. washwashed twice with tBuOMe
  7. customdried

Sources & evidence

ORD record
ord-c056fe1995cc4613a6b1576f786904c3
Source dataset
uspto-grants-2016_08
Patent number
US09408392B2

Reaction notes

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