Methanol → HCID 58006707, compound

HRID 80930Notes

Reaction equation

HRID 80930 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][N:8]([C:11]3[N:16]=[CH:15][C:14]([C:17]4[CH:24]=[CH:23][C:20]([C:21]#N)=[CH:19][CH:18]=4)=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.CC(C[AlH]CC(C)C)C.C[OH:35].[OH-].[Na+]>C1COCC1.O>[CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][N:8]([C:11]3[N:16]=[CH:15][C:14]([C:17]4[CH:24]=[CH:23][C:20]([CH:21]=[O:35])=[CH:19][CH:18]=4)=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 887MethanolHCID 14487Diisobutylaluminum hydrideHCID 14798Sodium HydroxideHCID 580066674-(6-(4-Cyclopropylmethylpiperazin-1-yl)-pyridin-3-yl)-benzonitrile

Product 1

HCID 58006707HCID 58006707, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of 4-[6-(4-cylopropylmethyl-piperazin-1-yl)-pyridin-3-yl]-benzonitrile (2.0 g, 6.3 mmol) dissolved in THF (40 mL) was added DIBAL-H (25 mL, 1 N) at −40° C. The mixture was stirred 2 h at −40° C. and then CH3OH (15 mL), water (100 mL) and 1 N NaOH (15 mL) was added at −40° C. The mixture was extracted with EtOAc (3×300 mL). The combined organic extracts were washed with water (3×50 mL), dried (Na2SO4) and concentrated under reduced pressure to give 1.7 g (51%) of 4-[6-(4-cyclopropylmethyl-piperazin-1-yl)-pyridin-3-yl]-benzaldehyde.

Workup

  1. extractionThe mixture was extracted with EtOAc (3×300 mL)
  2. washThe combined organic extracts were washed with water (3×50 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7cd4c4b1836f4634870ed12f09e8828d
Source dataset
uspto-grants-2014_09
Patent number
US08846677B2

Reaction notes

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