Oxirane, ((4-nitrophenoxy)methyl)-, (R)- → HCID 15675897, compound

HRID 1091098Notes

Reaction equation

HRID 1091098 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 147858Oxirane, ((4-nitrophenoxy)methyl)-, (R)-HCID 15675896N-Methyl-1-(quinolin-2-yl)methanamine

Product 1

HCID 15675897HCID 15675897, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
60 °C

Procedure

2-(Methylaminomethyl)quinoline (5.57 g, 32.41 mmol) in acetonitrile (30 mL) was added to a stirring solution of (R)-(-)-2-[(4-nitrophenoxy)methyl]oxirane (6.32 g, 32.41 mmol) in acetonitrile (90 mL) and the mixture was stirred 18 hours at 60° C., then 48 hours at 20° C. The solvent was removed in vacuo, and the residue was partitioned between ethyl acetate/brine. The organic layer was dried, decolorized, and concentrated to afford crude product which was used directly in the next step.

Workup

  1. custom48 hours
  2. customat 20° C
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between ethyl acetate/brine
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customto afford crude product which

Sources & evidence

ORD record
ord-9a14cec7216045a998f09db8f97d5456
Source dataset
uspto-grants-1992_01
Patent number
US05084463

Reaction notes

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