Acetic Acid → HCID 28423879, compound

HRID 1191010Notes

Reaction equation

HRID 1191010 reaction equation
C([BH3-])#N.[Na+].[C:5]([C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1)#[N:6].[CH:15]1([NH2:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(O)(=O)C.[OH-].[Na+]>CO.O>[CH:15]1([NH:21][CH2:11][C:10]2[CH:13]=[CH:14][C:7]([C:5]#[N:6])=[CH:8][CH:9]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 7965CyclohexylamineHCID 14798Sodium HydroxideHCID 660424-CyanobenzaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 28423879HCID 28423879, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Under a nitrogen atmosphere, add sodium cyanoborohydride (9.6 g, 152 mmol) to a solution of 4-cyanobenzaldehyde (5 g, 38 mmol), cyclohexylamine (3.8 g, 38 mmol) and acetic acid (0.46 g, 7.6 mmol) in methanol (100 mL) at 0° C. Warm the mixture to room temperature and stir overnight. Add water (100 mL) and adjust the pH to 10 with 3N aqueous NaOH. Extract with DCM and wash the organic phase with water and brine. Dry the organic phase over Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel (500 g) eluting with hexane/EtOAc (1:0 to 1:1 gradient) to obtain the desired intermediate (6.9 g, 86%). MS (APCI+) m/z: 215 (M+H)+.

Workup

  1. extractionExtract with DCM
  2. washwash the organic phase with water and brine
  3. dry with materialDry the organic phase over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify by chromatography on silica gel (500 g)
  7. washeluting with hexane/EtOAc (1:0 to 1:1 gradient)

Sources & evidence

ORD record
ord-57baa315b1dc492d821dea19ed45a6fc
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

Loading…