4-Fluorobenzylamine → HCID 10405113, compound

HRID 852286Notes

Reaction equation

HRID 852286 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.O=[C:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:13][CH2:12]1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[CH2:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][CH:11]([NH:7][CH2:6][C:5]2[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:12][CH2:13]1)=[O:18])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 673264-FluorobenzylamineHCID 643496Benzyl 4-oxopiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 10405113HCID 10405113, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

A solution of 4-fluorobenzylamine (5.48 g, 43.8 mmol) in a mixture of methanol and acetic acid (5:1, 60 mL) was added dropwise to a solution of benzyl 4-oxo-1-piperidine carboxylate (10.2 g, 43.8 mmol) in methanol (150 mL) at rt. To this mixture sodium cyanoborohydride (5.50 g, 87.5 mmol) was slowly added. After 20 hours stirring at rt the reaction mixture was neutralized and the solvent was removed by evaporation under reduced pressure. The residue was partitioned between dichloromethane and water. The organic layer was dried over sodium sulphate, filtered and evaporated to dryness. Purification of the residue by silica gel column chromatography, eluting with 7% methanol in dichloromethane, afforded the desired compound (9.0 g, 60%).

Workup

  1. customthe solvent was removed by evaporation under reduced pressure
  2. customThe residue was partitioned between dichloromethane and water
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customPurification of the residue by silica gel column chromatography
  7. washeluting with 7% methanol in dichloromethane

Sources & evidence

ORD record
ord-34f4a452843842368d0693f8b0c2a480
Source dataset
uspto-grants-2007_08
Patent number
US07253186B2

Reaction notes

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