Sodium cyanoborohydride → HCID 66798579, compound

HRID 1193387Notes

Reaction equation

HRID 1193387 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([O:7][CH:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)=[CH:3][CH:2]=1.CN.Cl.[BH3-][C:19]#[N:20].[Na+]>CO>[CH3:19][NH:20][CH:11]1[CH2:12][CH2:13][CH:8]([O:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 66799314HCID 66799314, compound

Product 1

HCID 66798579HCID 66798579, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(Pyridin-4-yloxy)cyclohexanone (1.15 g, 6.052 mmol, 1.0 eq.) was dissolved in MeOH (15 ml); CH3NH2.HCl (490 mg, 7.263 mmol, 1.2 eq.) was added and stirring was carried out for 3 hours at RT. NaCNBH3 (760 mg, 12.105 mmol, 2.0 eq.) was added in portions at 0° C. and the mixture was stirred for 16 hours at RT. After monitoring by TLC, the reaction mixture was concentrated under reduced pressure and the residue was taken up in water (50 ml) and extracted with 10% MeOH in DCM (2×75 ml). The combined org. phases were dried over sodium sulfate, concentrated and purified by column chromatography (Alox, 3% MeOH in DCM). Yield: 21% (270 mg, 1.310 mmol)

Workup

  1. stirringthe mixture was stirred for 16 hours at RT
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. extractionextracted with 10% MeOH in DCM (2×75 ml)
  4. dry with materialphases were dried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by column chromatography (Alox, 3% MeOH in DCM)

Sources & evidence

ORD record
ord-3ac85e2da32c4a448b0db43b64f8b899
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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