Acetic Acid → HCID 89922873, compound

HRID 921833Notes

Reaction equation

HRID 921833 reaction equation
[NH2:1][C:2]1[C:3]([Cl:14])=[CH:4][C:5]([CH2:10][CH2:11][CH:12]=O)=[C:6]([CH:9]=1)[C:7]#[N:8].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C([BH3-])#N.[Na+].C(O)(=O)C>C1COCC1>[NH2:1][C:2]1[C:3]([Cl:14])=[CH:4][C:5]([CH2:10][CH2:11][CH2:12][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 89922720HCID 89922720, compound

Product 1

HCID 89922873HCID 89922873, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-amino-4-chloro-2-(3-oxopropyl)benzonitrile (50 mg, 0.240 mmol, Example 566A) in THF (0.5 mL) at room temperature was added morpholine (37.6 mg, 0.431 mmol), sodium cyanoborohydride (30.1 mg, 0.479 mmol), and a drop of acetic acid. The reaction was stirred at room temperature for 1 h at which point LCMS indicated full conversion. The reaction was quenched with aq. Na2CO3 and extracted with DCM. The organic layer was dried over Na2SO4, filtered, and concentrated. The crude material was purified by flash column chromatography (0-10% MeOH/DCM) to give 5-amino-4-chloro-2-(3-morpholinopropyl)benzonitrile (54 mg) as yellow oil.

Workup

  1. customThe reaction was quenched with aq. Na2CO3
  2. extractionextracted with DCM
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by flash column chromatography (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-c5c1c225f2f64404906095d9ca4421ab
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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