Acetic Acid → HCID 66799229, compound

HRID 1193343Notes

Reaction equation

HRID 1193343 reaction equation
C(O)(=O)C.[N:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1.Cl.CN.[BH3-][C:22]#[N:23].[Na+]>CO>[CH3:22][NH:23][CH:14]1[CH2:15][CH2:16][CH:11]([C:8]2[CH:9]=[CH:10][N:5]=[CH:6][CH:7]=2)[CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 10154273Cyclohexanone, 4-(4-pyridinyl)-

Product 1

HCID 66799229HCID 66799229, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetic acid (0.2 ml) was added catalytically to an ice-cooled (0° C.) solution of 4-(pyridin-4-yl)cyclohexanone (500 mg, 2.857 mmol, 1 eq) and methylamine hydrochloride (957 mg, 14.28 mmol, 5 eq) in MeOH (10 ml), and stirring was carried out for 1 h at RT. NaCNBH3 (358 mg, 5.714 mmol, 2 eq) was added at 0° C. and stirring was carried out for a further 14 h at RT. The reaction mixture was concentrated, diluted with dichloromethane (100 ml) and washed with sat. sodium hydrogen carbonate solution (60 ml) and sat. NaCl solution (60 ml). The organic phase was dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (Alox neutral, 6% MeOH in dichloromethane). The desired amine was obtained in the form of a light-yellow solid. Yield: 27% (150 mg, 1.26 mmol).

Workup

  1. stirringstirring
  2. waitwas carried out for a further 14 h at RT
  3. concentrationThe reaction mixture was concentrated
  4. additiondiluted with dichloromethane (100 ml)
  5. washwashed with sat. sodium hydrogen carbonate solution (60 ml) and sat. NaCl solution (60 ml)
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. custompurified by column chromatography (Alox neutral, 6% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-a5f830703c514afdbf96bd96f1cedb6f
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

Loading…