Acetic Acid → HCID 89922616, compound

HRID 921844Notes

Reaction equation

HRID 921844 reaction equation
[NH2:1][C:2]1[C:3]([Cl:15])=[CH:4][C:5]([CH2:10][CH2:11][CH2:12][CH:13]=O)=[C:6]([CH:9]=1)[C:7]#[N:8].[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C([BH3-])#N.[Na+].C(O)(=O)C>C1COCC1>[NH2:1][C:2]1[C:3]([Cl:15])=[CH:4][C:5]([CH2:10][CH2:11][CH2:12][CH2:13][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 89922748HCID 89922748, compound

Product 1

HCID 89922616HCID 89922616, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-amino-4-chloro-2-(4-oxobutyl)benzonitrile (35 mg, 0.157 mmol) in THF (0.5 mL) at room temperature was added morpholine (24.65 mg, 0.283 mmol), sodium cyanoborohydride (19.76 mg, 0.314 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, extracted w/ DCM, concentrated and purified by flash column chromatography (0-10% MeOH/DCM) to give 5-amino-4-chloro-2-(4-morpholinobutyl)benzonitrile (29 mg) as a yellow oil.

Workup

  1. customThe reaction was quenched with aq. Na2CO3
  2. extractionextracted w/ DCM
  3. concentrationconcentrated
  4. custompurified by flash column chromatography (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-8808ac3812f644ef8df1820d252a7c47
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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