Potassium Iodide → HCID 10538587, compound

HRID 2168210Notes

Reaction equation

HRID 2168210 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][CH2:5]1.[OH:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=1)[C:13]([O:15][CH3:16])=[O:14].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N:4]1([CH2:3][CH2:2][O:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15][CH3:16])=[O:14])[CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 816691-(2-Chloroethyl)pyrrolidineHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 10538587HCID 10538587, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 1-(2-chloroethyl)pyrrolidine D36 (9.2 g) and methyl 3-hydroxybenzoate (12.5 g, 82 mmol) and potassium iodide (13.68 g, 82 mmol) and potassium carbonate (11.37 g, 82 mmol) in acetone (200 ml) was refluxed for 2 days. The reaction was filtered and concentrated to give crude product which was purified by chromatography on silica gel eluting with pet eth/EtOAc 5/1 and EtOAc and MeOH to give 1.6 g of desired product D37 as a brown product. LCMS [MH+] 250.1 g 1.53 min (5 min run)

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. customto give crude product which
  4. customwas purified by chromatography on silica gel eluting with pet

Sources & evidence

ORD record
ord-10230a68a96b4d3f9b395fa3296060cc
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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