Pyrrolidine → HCID 68532473, compound

HRID 644227Notes

Reaction equation

HRID 644227 reaction equation
F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)[CH:3]=1.[NH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>>[CH3:19][N:16]1[CH2:17][CH2:18][CH:13]([O:12][C:4]2[CH:3]=[C:2]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:11]=[CH:10][C:5]=2[C:6]([O:8][CH3:9])=[O:7])[CH2:14][CH2:15]1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 68535529HCID 68535529, compound

Product 1

HCID 68532473HCID 68532473, compoundYield 93%

Conditions

Temperature
70 °C

Procedure

The methyl 4-fluoro-2-(1-methylpiperidin-4-yloxy)benzoate (10.6 g, 40 mmol) was mixed with pyrrolidine (14 g, 200 mmol) and heated at 70° C. for 3 hours, then heated at 100° C. for 1 hour before concentrating under vacuum. The residue was partitioned between EtOAc (100 mL) and saturated aqueous NaHCO3 (100 mL). The aqueous layer was saturated with NaCl and extracted with EtOAc (100 mL). The combined organic layer was dried over MgSO4 and concentrated to 12.5 g of an oil which was purified by flash chromatography, using THF/Hex/Et3 N 20/75/5 then 40/55/5 and finally 60/35/5, to give 11.9 g (37 mmol, 93%) of the desired product as an oil.

Workup

  1. temperatureheated at 100° C. for 1 hour
  2. concentrationbefore concentrating under vacuum
  3. customThe residue was partitioned between EtOAc (100 mL) and saturated aqueous NaHCO3 (100 mL)
  4. extractionextracted with EtOAc (100 mL)
  5. dry with materialThe combined organic layer was dried over MgSO4
  6. concentrationconcentrated to 12.5 g of an oil which
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-4347ea1a8d254ebbb16bc5f4ac049827
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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