Dimethylformamide → HCID 21914371, compound

HRID 1245831Notes

Reaction equation

HRID 1245831 reaction equation
S(C1C=CC(C)=CC=1)(O[CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Br:14])(=O)=O.[F:22][C:23]1([F:29])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[F:22][C:23]1([F:29])[CH2:28][CH2:27][N:26]([CH2:5][CH2:6][O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Br:14])[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27583524,4-DifluoropiperidineHCID 11100743HCID 11100743, compound

Product 1

HCID 21914371HCID 21914371, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

2-(2-Bromophenoxy)ethyl tosylate (1.86 g), 4,4-difluoropiperidine (0.73 g) and potassium carbonate (0.97 g) were mixed with dimethylformamide (30 ml) and heated to 60° C. for 18 h. The mixture was cooled and added to water (300 ml). The mixture was extracted with diethyl ether (×3), dried and evaporated. Purification was achieved using cation exchange chromatography eluting with ammonia/methanol/dichloromethane mixtures yielding, 4-difluoro-(2-(2-bromophenoxy)ethyl)piperidine (0.77 g).

Workup

  1. temperatureThe mixture was cooled
  2. extractionThe mixture was extracted with diethyl ether (×3)
  3. customdried
  4. customevaporated
  5. customPurification
  6. washeluting with ammonia/methanol/dichloromethane mixtures
  7. customyielding

Sources & evidence

ORD record
ord-7f35c1505ac54da3841468653def73a8
Source dataset
uspto-grants-2006_10
Patent number
US07125896B2

Reaction notes

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