Hydrochloric Acid → 6-(4-Fluorophenyl)-3-azabicyclo[4.1.0]heptane

HRID 2426722Notes

Reaction equation

HRID 2426722 reaction equation
[CH2:1]([Zn]CC)C.FC(F)(F)C(O)=O.ICI.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH2:24][CH2:25][NH:26][CH2:27][CH:28]=2)=[CH:19][CH:18]=1.Cl>ClCCl>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]23[CH2:1][CH:24]2[CH2:25][NH:26][CH2:27][CH2:28]3)=[CH:19][CH:18]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6346DiiodomethaneHCID 6422Trifluoroacetic acidHCID 1977484-(4-Fluorophenyl)-1,2,3,6-tetrahydropyridineHCID 178418750HCID 178418750, compound

Product 1

HCID 211055316-(4-Fluorophenyl)-3-azabicyclo[4.1.0]heptane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Diethylzinc (1M in hexane, 19 ml) in dichloromethane (100 ml) was mixed with trifluoroacetic acid (3 ml) at 0C. After 20 minutes, diiodomethane (3 ml) in dichloromethane (10 ml) was added. Then 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine (3.0 g) in dichloromethane (10 ml) was added, and the mixture was stirred at room temperature overnight. After addition of hydrochloric acid (1N), the phases were separated and the organic phase was washed with water, dried over magnesium sulfate and concentrated. This resulted in the product with the molecular weight of 191.25 (C12H14FN); MS (ESI): 192 (M+H+).

Workup

  1. customthe phases were separated
  2. washthe organic phase was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThis resulted in the product with the molecular weight of 191.25 (C12H14FN)

Sources & evidence

ORD record
ord-e58938c0f2de42619585c1b9593371e3
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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