Iodoethane → HCID 25145775, compound

HRID 1931796Notes

Reaction equation

HRID 1931796 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:14])[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].C(=O)([O-])[O-].[K+].[K+].I[CH2:22][CH3:23]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:14])[CH2:13][CH2:12][N:11]([CH2:22][CH3:23])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 685178373-(3-Chloro-4-fluorophenyl)pyrrolidin-3-ol

Product 1

HCID 25145775HCID 25145775, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation according to Example 2: 3-(3-chloro-4-fluorophenyl)pyrrolidin-3-ol (0.31 g, 1.46 mmol), acetonitrile (3 mL), potassium carbonate (0.20 g, 1.46 mmol), iodoethane (0.12 mL, 1.5 mmol). Microwave irradiation at 100° C. for 20 minutes. Purification by HPLC on Waters OBD C18, 5 μm (MeOH/33 mM NH3, 55:45). Yield: 0.19 g. The amine was converted to the fumaric acid salt and recrystallized from ethanol/diethyl ether/diisopropyl ether: M.p. 157-158° C.; MS m/z (relative intensity, 70 eV) 243 (M+, 9), 228 (9), 157 (13), 129 (10), 71 (bp).

Workup

  1. customPreparation
  2. customMicrowave irradiation at 100° C. for 20 minutes
  3. customPurification by HPLC on Waters OBD C18, 5 μm (MeOH/33 mM NH3, 55:45)
  4. customrecrystallized from ethanol/diethyl ether/diisopropyl ether

Sources & evidence

ORD record
ord-bcd85ace929c4a0ebdb3ef998f892af9
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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