Hydrochloric Acid → HCID 67065050, compound

HRID 535800Notes

Reaction equation

HRID 535800 reaction equation
[Br:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([C@@H:14]3[CH2:16][C@H:15]3[NH:17]C(=O)OC(C)(C)C)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([C@@H:14]3[CH2:16][C@H:15]3[NH2:17])=[CH:10][CH:9]=2)=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 67064921HCID 67064921, compound

Product 1

HCID 67065050HCID 67065050, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl(trans)-2-(4-(4-bromobenzyloxy)phenyl)cyclopropylcarbamate (11 g, 26.37 mmol) in dioxane (110 mL) at 0° C., HCl in Dioxane (110 mL) was added and stirred for 1 h. After completion, the solvent was evaporated and residue was triturated with Et2O (15 mL) to give crude salt. The crude salt was dissolved in water (150 mL), basified with Na2CO3 solution, extracted with EtOAc (3×100 mL). The combined extracts were washed with water (50 mL), brine (50 mL), dried over anhydrous Na2SO4, filtered and evaporated to get (8.2 g, 98%) (trans)-2-(4-(4-bromobenzyloxy)phenyl)cyclopropanamine

Workup

  1. customAfter completion, the solvent was evaporated
  2. customresidue was triturated with Et2O (15 mL)
  3. customto give crude salt
  4. extractionextracted with EtOAc (3×100 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-e635d1405d3a4204bca3c56d14d26811
Source dataset
uspto-grants-2014_10
Patent number
US08859555B2

Reaction notes

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