Sodium Carbonate → HCID 69829839, compound

HRID 1386949Notes

Reaction equation

HRID 1386949 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6](CBr)[CH:5]=1.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.[C:18]([O-])([O-])=O.[Na+].[Na+].[ClH:24].CC(O)C>C1(C)C=CC=CC=1.CC#N.CCOC(C)=O>[ClH:24].[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=1[CH2:18][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 31268PyrrolidineHCID 517981Methyl 3-(bromomethyl)benzoateHCID 21912024Isopropanol hydrochloride

Product 1

HCID 69829839HCID 69829839, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl-3-(bromomethyl)benzoate (7 g, 30.5 mmol) in toluene (170 ml) was heated with pyrrolidine (4.5 g, 64.1 mmol, 2.1 eq.) for at 80° C. for 17 hrs. After addition of Na2CO3, and extraction of the aqueous phase with EtOAc, the organic phase was washed with brine and dried with Na2SO4 Solvent evaporation then afforded the crude product as a yellow oil. This material was dissolved in MeCN and a slight excess of 6N HCl/iPrOH added. After stirring for 30 min. the hydrochloride salt was filtered off and washed with ether to afford the title compound (5 g, 19.5 mmol, 64% yield) as a white solid. MS: m/e=219 (M+).

Workup

  1. washthe organic phase was washed with brine
  2. dry with materialdried with Na2SO4 Solvent evaporation
  3. customthen afforded the crude product as a yellow oil
  4. filtrationwas filtered off
  5. washwashed with ether

Sources & evidence

ORD record
ord-ac3fb33572554dd092fdc9825177bc9a
Source dataset
uspto-grants-2001_07
Patent number
US06265426B1

Reaction notes

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