Borane → HCID 68761225, compound

HRID 970232Notes

Reaction equation

HRID 970232 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=O)([O-:3])=[O:2].B>C1COCC1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][N:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6331Borane2×HCID 827569HCID 827569, compound

Product 1

HCID 68761225HCID 68761225, compoundYield 120.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 4-[(2-nitrophenyl)acetyl]morpholine (10 g, 40 mmol) in THF (250 ml) was added borane. THF (1.0M, 60 ml, 60 mmol) and the mixture heated at reflux for 1 h. A further portion of borane. THF (1.0M, 80 ml, 80 mmol) was added and reflux continued for 1 h. The cooled reaction was quenched by addition of hydrochloric acid (concentrated, 8 ml) and left at room temperature for 18 h. The mixture was concentrated under vacuum, basified with aqueous sodium hydroxide (2N) and extracted with ether (3×100 ml). The combined extracts were dried (magnesium sulphate) and the solvent evaporated under vacuum to give a crude sample of 4-[(2-nitrophenyl)ethyl]morpholine (11.42 g), which was used without further purification. Microanalysis: calculated C 61.007, H 6.83, N 11.86; found C 62.38; H, 8.02; N, 9.54.

Workup

  1. temperatureat reflux for 1 h
  2. temperaturereflux
  3. customThe cooled reaction
  4. customwas quenched by addition of hydrochloric acid (concentrated, 8 ml)
  5. waitleft at room temperature for 18 h
  6. concentrationThe mixture was concentrated under vacuum
  7. extractionextracted with ether (3×100 ml)
  8. dry with materialThe combined extracts were dried (magnesium sulphate)
  9. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-32a173a847b94456aa2fe1ef3438cf7d
Source dataset
uspto-grants-2007_12
Patent number
US07309800B2

Reaction notes

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