Hydrochloric Acid → HCID 44398212, compound

HRID 1916027Notes

Reaction equation

HRID 1916027 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:10][C:9]1([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[F:11])(C)(C)C.Cl.O>CO.C(O)C>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([C:9]2([F:11])[CH2:10][CH:8]2[NH2:7])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 59161499HCID 59161499, compound

Product 1

HCID 44398212HCID 44398212, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

(2-(4-chlorophenyl)-2-fluoro-cyclopropyl)-carbamic acid tert-butyl ester from example P5c) (1.00 g; 3.5 mmol) was dissolved in methanol (10 ml) and a saturated solution of HCl in ethanol (10 ml) added. The solution was stirred at room temperature for 2 h then evaporated leaving a white solid. Water (50 ml) then added and mixture extracted twice with ethyl acetate. The aqueous phase was made alkaline with 2M NaOH and extracted twice with ethyl acetate. The extracts were dried (MgSO4) and evaporated. 0.60 g of 2-(4-chlorophenyl)-2-fluoro-cyclopropylamine was obtained in the form of a yellow oil (92% of theory) as a 7:3 mixture of cis/trans isomers.

Workup

  1. customthen evaporated
  2. customleaving a white solid
  3. extractionmixture extracted twice with ethyl acetate
  4. extractionextracted twice with ethyl acetate
  5. dry with materialThe extracts were dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-d57861fe324940598ab53668c8c81914
Source dataset
uspto-grants-2013_12
Patent number
US08618023B2

Reaction notes

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