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

HRID 1677145Notes

Reaction equation

HRID 1677145 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 (1.0 mmol) and n-methylmorpholine (1.0 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-0523f50f81954282b5c2d7861c1cb998
Source dataset
uspto-grants-2011_08
Patent number
US08008301B2

Reaction notes

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