(S)-2-((4-Nitrophenoxy)methyl)oxirane → HCID 15675898, compound

HRID 1091099Notes

Reaction equation

HRID 1091099 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[N+:14]([C:17]1[CH:27]=[CH:26][C:20]([O:21][CH2:22][C@@H:23]2[CH2:25][O:24]2)=[CH:19][CH:18]=1)([O-:16])=[O:15]>C(#N)C>[CH3:1][N:2]([CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH2:25][C@H:23]([OH:24])[CH2:22][O:21][C:20]1[CH:19]=[CH:18][C:17]([N+:14]([O-:16])=[O:15])=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 147859(S)-2-((4-Nitrophenoxy)methyl)oxiraneHCID 15675896N-Methyl-1-(quinolin-2-yl)methanamine

Product 1

HCID 15675898HCID 15675898, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

2-(Methylaminomethyl)quinoline (4.47 g, 25.96 mmol) in acetonitrile (30 mL) was added to a stirring solution of (S)-(+)-2-[(4-nitrophenoxy)methyl]oxirane (4.23 g, 21.67 mmol) in acetonitrile (10 mL). The reaction was lightly refluxed under N2 for 24 hours, cooled and concentrated in vacuo. The residue was purified by HPLC dried and heated under vacuum to afford 5.01 g (63%) of product which was used directly in the next step.

Workup

  1. temperatureThe reaction was lightly refluxed under N2 for 24 hours
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by HPLC
  5. customdried
  6. temperatureheated under vacuum

Sources & evidence

ORD record
ord-6847ff37c591445ab622d664ab303cb7
Source dataset
uspto-grants-1992_01
Patent number
US05084463

Reaction notes

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