Hydrochloric Acid → HCID 22141218, compound

HRID 1826422Notes

Reaction equation

HRID 1826422 reaction equation
Cl[CH2:2][CH:3]1[CH:5]([C:6]([O:8]CC)=O)[C:4]1([CH3:20])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl>>[CH2:21]([N:28]1[CH2:2][CH:3]2[CH:5]([C:4]2([CH3:20])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:6]1=[O:8])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 22141336Ethyl 3-(chloromethyl)-2-methyl-2-(3-nitrophenyl)cyclopropanecarboxylate

Product 1

HCID 22141218HCID 22141218, compoundYield 55.4%

Procedure

A solution of ethyl 3-(chloromethyl)-2-methyl-2-(3-nitrophenyl)cyclopropane carboxylate (Preparation 5, 10 g, 33.6 mmol) in benzylamine (21.6 g, 201.6 mmol) was heated to 160° C. for 16 h. The mixture was cooled, 2N hydrochloric acid was added (200 ml), and the mixture was extracted with dichloromethane (3×250 ml). The combined extracts were dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by silica (600 g) column chromatography eluting with dichloromethane, then a gradient of dichloromethane:ethyl acetate ending with pure ethyl acetate. Appropriate fractions were combined and concentrated in vacuo to give the title compound as an amber oil (6 g, 55%).

Workup

  1. temperatureThe mixture was cooled
  2. extractionthe mixture was extracted with dichloromethane (3×250 ml)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica (600 g) column chromatography
  7. washeluting with dichloromethane
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d067b6c473fd46aba654494de317fb1e
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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