Hydrochloric Acid → HCID 66715451, compound

HRID 535802Notes

Reaction equation

HRID 535802 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]3[CH2:17][C@H:16]3[NH:18]C(=O)OC(C)(C)C)=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.Cl.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)C.O>[F:1][C:2]([F:26])([F:27])[C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]3[CH2:17][C@H:16]3[NH2:18])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 86673371Tert-butyl(trans)-2-(3'-(trifluoromethyl)biphenyl-4-yl)cyclopropylcarbamate

Product 1

HCID 66715451HCID 66715451, compoundYield 98.09%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of tert-butyl(trans)-2-(3′-(trifluoromethyl)biphenyl-4-yl)cyclopropylcarbamate (5 g) in diethyl ether (50 mL) at 0° C., HCl in Diethyl ether (20 mL) was added and stirred for 1 h. After completion, the solvent was evaporated and residue was triturated with Et2O (20 mL) to give crude salt. The crude salt was dissolved in water (50 mL), basified with Na2CO3 solution, extracted with EtOAc (3×50 mL). The combined extracts were washed with water (50 mL), brine (50 mL), dried over anhydrous Na2SO4, filtered and evaporated to get crude (trans)-2-(3′-(trifluoromethyl)biphenyl-4-yl)cyclopropanamine (3.6 g, 98.09%) as a white solid

Workup

  1. customAfter completion, the solvent was evaporated
  2. customresidue was triturated with Et2O (20 mL)
  3. customto give crude salt
  4. extractionextracted with EtOAc (3×50 mL)
  5. washThe combined extracts were washed with water (50 mL), brine (50 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-17345fa214fb4361896109ce25a29d19
Source dataset
uspto-grants-2014_10
Patent number
US08859555B2

Reaction notes

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