Water → HCID 67107904, compound

HRID 1910814Notes

Reaction equation

HRID 1910814 reaction equation
O.[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)([O-:4])=[O:3].[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.C([BH3-])#N.[Na+]>O1CCCC1.C(O)(=O)C>[N+:2]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:12][CH2:13][N:14]([C:17]3[CH:24]=[CH:23][C:20]([CH2:21][N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[CH:19][CH:18]=3)[CH2:15][CH2:16]2)=[CH:9][CH:10]=1)([O-:4])=[O:3]

Participants

7

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 45920966HCID 45920966, compound

Product 1

HCID 67107904HCID 67107904, compoundYield 52.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of water (1 mL), acetic acid (1 mL), 4-[4-(4-nitro-phenyl)-piperazin-1-yl]-benzaldehyde (700 mg, 2.25 mmol) and morpholine (215 mg, 2.47 mmol) in tetrahydrofuran (10 mL) was stirred at room temperature for 1 h. Sodium cyanoborohydride (212 mg, 3.37 mmol) was added at room temperature then the mixture was heated at reflux for 10 h. The tetrahydrofuran was removed in vacuo and the residue was partitioned between water and ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate and evaporated in vacuo to afford a residue which was purified by column chromatography on silica gel (60-120 mesh) using 1% methanol in chloroform as eluent to afford 4-{4-[4-(4-nitro-phenyl)-piperazin-1-yl]-benzyl}-morpholine (450 mg, 52%) as a brownish yellow solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 10 h
  3. customThe tetrahydrofuran was removed in vacuo
  4. customthe residue was partitioned between water and ethyl acetate
  5. washThe organic layer was washed with saturated sodium bicarbonate solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated in vacuo
  8. customto afford a residue which
  9. customwas purified by column chromatography on silica gel (60-120 mesh)

Sources & evidence

ORD record
ord-63f73c83a0b847f29f67c04dca369fd8
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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