Water → HCID 24904659, compound

HRID 1804711Notes

Reaction equation

HRID 1804711 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1.[CH2:12]([N:14](CC)[CH2:15][CH3:16])[CH3:13].[OH2:19]>C(#N)C>[N+:9]([C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH2:2][N:14]1[CH2:15][CH2:16][CH:13]([OH:19])[CH2:12]1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 77568Benzene, 1-(bromomethyl)-3-nitro-

Product 1

HCID 24904659HCID 24904659, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 25 mL round bottom was charged with 1-(bromomethyl)-3-nitrobenzene (542 mg, 2.509 mmol) pyrrolidin-3-ol (0.813 mL, 10.04 mmol), and triethylamine (1.399 mL, 10.04 mmol) in acetonitrile (5 mL). The resulting solution was stirred overnight at ambient temperature then poured into water (150 mL) and extracted with CH2Cl2 (4×30 mL). The extracts were washed with sat. NaHCO3 solution, H2O and brine. The organic layer was then dried (Na2SO4) and concentrated in vacuo, yielding the title compound. MS (ESI(+)) m/e 222.9 (M+H)+.

Workup

  1. extractionextracted with CH2Cl2 (4×30 mL)
  2. washThe extracts were washed with sat. NaHCO3 solution, H2O and brine
  3. dry with materialThe organic layer was then dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-231e20a127a3422cbaa7dc7c67584ac7
Source dataset
uspto-grants-2013_01
Patent number
US08354422B2

Reaction notes

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