4-Methylmorpholine → (4-Bromo-2-fluoro-phenyl)-(2-pyrrolidin-1-ylmethyl-pyrrolidin-yl)methanone

HRID 1867801Notes

Reaction equation

HRID 1867801 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[CH2:6][N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.CN1CCOCC1.[Br:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[C:22]([F:29])[CH:21]=1>ClCCl>[Br:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([N:1]2[CH2:5][CH2:4][CH2:3][CH:2]2[CH2:6][N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)=[O:25])=[C:22]([F:29])[CH:21]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 27340264-Bromo-2-fluorobenzoyl chloride

Product 1

HCID 11966062(4-Bromo-2-fluoro-phenyl)-(2-pyrrolidin-1-ylmethyl-pyrrolidin-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Procedure DD: To a stirring solution of (S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (11.0 mmol) and n-methylmorpholine (11.0 mmol) in dichloromethane (0.10M), slowly add 4-Bromo-2-fluorobenzoic acid chloride (1.0 mmol) diluted in dichloromethane. Stir reaction at room temperature for one hour. After this time wash the reaction with saturated aqueous sodium bicarbonate while extracting with dichloromethane. Dry the organic layer with sodium sulfate, filter and concentrate in vacuo to give the title compound. MS (m/e): 355.1/357.1 (M+1)

Workup

  1. customreaction at room temperature for one hour
  2. washAfter this time wash
  3. customthe reaction with saturated aqueous sodium bicarbonate
  4. extractionwhile extracting with dichloromethane
  5. dry with materialDry the organic layer with sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-f0bb289ae1c54c518a0ce6b5fd692a78
Source dataset
uspto-grants-2009_12
Patent number
US07632857B2

Reaction notes

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