Morpholine → HCID 66878419, compound

HRID 880483Notes

Reaction equation

HRID 880483 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[N:27]=[CH:26][C:25]([CH:28]=O)=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)([O-:9])=[O:8].C([BH3-])#N.[Na+]>O1CCCC1.C(O)(=O)C.C(Cl)(Cl)Cl>[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[N:27]=[CH:26][C:25]([CH2:28][N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)([O-:9])=[O:8]

Participants

7

Reactant 3

HCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 86654676HCID 86654676, compound

Product 1

HCID 66878419HCID 66878419, compoundYield 59.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

Morpholine (250 mg, 2.87 mmol) was added to a suspension of 6-[4-(4-nitrophenyl)piperazin-1-yl]pyridine-3-carbaldehyde (750 mg, 2.41 mmol) and sodium cyanoborohydride (454 mg, 7.23 mmol) in a mixture of tetrahydrofuran (10 mL) and acetic acid (0.5 mL) at ambient temperature then heated at reflux for 3 h. The mixture was then concentrated in vacuo to give a gummy solid which was dissolved in chloroform (40 mL), washed with water (2×20 mL), brine (2×15 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give the crude compound. Purification by column chromatography over neutral alumina using 20-30% of ethyl acetate in petroleum ether afforded 4-[[6-[4-(4-nitrophenyl)piperazin-1-yl]-3-pyridyl]methyl]morpholine (550 mg, 59%).

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 3 h
  3. concentrationThe mixture was then concentrated in vacuo
  4. customto give a gummy solid which
  5. washwashed with water (2×20 mL), brine (2×15 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto give the crude compound
  9. customPurification by column chromatography over neutral alumina using 20-30% of ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-db2c137367ef46f4b749dff09657171a
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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