Dimethylamine → HCID 71138946, compound

HRID 1914051Notes

Reaction equation

HRID 1914051 reaction equation
C(Cl)(=O)C(Cl)=O.[Br:7][C:8]1[CH:9]=[C:10]([N:14]2[CH2:18][CH2:17][CH:16]([C:19]([OH:21])=O)[CH2:15]2)[CH:11]=[CH:12][CH:13]=1.[CH3:22][N:23](C)[CH:24]=O.N(C)C>ClCCCl.C1COCC1.C1(C)C=CC=CC=1>[Br:7][C:8]1[CH:9]=[C:10]([N:14]2[CH2:18][CH2:17][CH:16]([C:19]([N:23]([CH3:24])[CH3:22])=[O:21])[CH2:15]2)[CH:11]=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 674DimethylamineHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 70900790HCID 70900790, compound

Product 1

HCID 71138946HCID 71138946, compoundYield 523.4%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

Oxalyl chloride (104 μL, 1.19 mmol) was added to a mixture of 1-(3-bromophenyl)pyrrolidine-3-carboxylic acid (293 mg, 1.08 mmol) and N,N-dimethylformamide (8.4 μL, 0.108 mmol) in DCE (5 mL). After heating the mixture at 65° C. for 2 hours, the mixture was coevaporated with toluene. The residue was diluted with THF (5 mL) and Me2NH (2M/THF, 2.71 mL, 5.42 mmol) was added to the mixture at 0° C. After stiffing the mixture for 16 hours at room temperature, the mixture was concentrated and the residue was diluted with water and extracted with EtOAc (3×). The combined organic layers were dried over anhydrous Na2SO4 and concentrated. The residue was purified by silica gel column chromatography (EtOAc/hexane=9:1→4:1→2:1) to afford desired product (168 mg, 48.0%) as orange oil.

Workup

  1. additionwas added to the mixture at 0° C
  2. customfor 16 hours
  3. customat room temperature
  4. concentrationthe mixture was concentrated
  5. additionthe residue was diluted with water
  6. extractionextracted with EtOAc (3×)
  7. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (EtOAc/hexane=9:1→4:1→2:1)

Sources & evidence

ORD record
ord-6b6534273e9844c596dbdf918a0f7a52
Source dataset
uspto-grants-2013_12
Patent number
US08609688B2

Reaction notes

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