Acetic Acid → HCID 59828914, compound

HRID 1191018Notes

Reaction equation

HRID 1191018 reaction equation
C([BH3-])#N.[Na+].[NH2:5][CH2:6][C:7]1[CH:8]=[N:9][C:10]([Cl:13])=[CH:11][CH:12]=1.[C:14]1(=O)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(O)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO.O>[Cl:13][C:10]1[N:9]=[CH:8][C:7]([CH2:6][NH:5][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:12][CH:11]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 7967CyclohexanoneHCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 70209275-(Aminomethyl)-2-chloropyridine

Product 1

HCID 59828914HCID 59828914, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Under a nitrogen atmosphere, add sodium cyanoborohydride (3.53 g, 56 mmol) to a solution of 3-aminomethyl-6-chloro-pyridine (2 g, 14 mmol), cyclohexanone (1.38 g, 14 mmol) and acetic acid (168 mg, 0.2 mmol) in methanol (20 mL) at 0° C. Warm the mixture to room temperature and stir overnight. Add water (100 mL) and saturated aqueous K2CO3. Extract three times with DCM and wash the combined organic extracts with water and brine. Dry over Na2SO4, filter, and concentrate in vacuo. Purify by chromatography on silica gel (150 g) eluting with 9:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) to obtain the desired intermediate (2.86 g, 91%). MS (APCI+) m/z: 225 (M+H)+.

Workup

  1. extractionExtract three times with DCM
  2. washwash the combined organic extracts with water and brine
  3. dry with materialDry over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify by chromatography on silica gel (150 g)
  7. washeluting with 9:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2)

Sources & evidence

ORD record
ord-e8ae77a896c5460e8a789fefb05ab195
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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