Acetic Acid → HCID 43123011, compound

HRID 1591866Notes

Reaction equation

HRID 1591866 reaction equation
[Cl:1][C:2]1[C:3]([F:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH3:10][N:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>>[CH3:10][N:11]1[CH2:16][CH2:15][CH:14]([NH:5][C:4]2[CH:6]=[CH:7][CH:8]=[C:2]([Cl:1])[C:3]=2[F:9])[CH2:13][CH2:12]1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 740491-Methyl-4-piperidoneHCID 750143-Chloro-2-fluoroanilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 43123011HCID 43123011, compoundYield 32.1%

Procedure

Combine 3-chloro-2-fluoroaniline (4.37 g, 30 mmol), 1-methylpiperidin-4-one (3.39 g, 30 mmol), sodium triacetoxyborohydride (5.26 g, 33 mmol), and acetic acid (5.4 g, 90 mmol) and stir at room temperature overnight. Partition the reaction mixture between dichloromethane and saturated aqueous NaCl containing NH4OH, dry over anhydrous sodium sulfate, evaporate and purify on a silica gel columnn (110 g), using a gradient of dichloromethane-2M NH3 in methanol to give 2.34 g of the title compound (32% yield): mass spectrum (ion spray): m/z=243 (M+1); 1H NMR (CDCl3): 6.88 (ddd,1H), 6.63 (ddd, 1H), 6.56 (dd, 1H), 3.85 (br d, 1H), 3.28 (m, 1H), 2.80 (m, 2H), 2.30 (s, 3H), 2.13 (m, 2H), 2.04 (m, 1H), 1.53 (m, 2H). (file: mn4-b6k-284-2)

Workup

  1. customPartition the reaction mixture between dichloromethane and saturated aqueous NaCl
  2. additioncontaining NH4OH
  3. dry with materialdry over anhydrous sodium sulfate
  4. customevaporate
  5. custompurify on a silica gel columnn (110 g)

Sources & evidence

ORD record
ord-b38fd34de0e74031880a7662e71f4d6e
Source dataset
uspto-grants-2007_11
Patent number
US07291632B2

Reaction notes

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