Acetic Acid → (1-Benzyl-piperidin-4-yl)-[5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-amine

HRID 1183336Notes

Reaction equation

HRID 1183336 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[NH2:14])=[CH:4][CH:3]=1.[CH2:15]([N:22]1[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH2:15]([N:22]1[CH2:27][CH2:26][CH:25]([NH:14][C:9]2[C:10]([CH3:13])=[N:11][O:12][C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 192201-Benzyl-4-piperidoneHCID 5003444Sodium cyanoborohydrideHCID 582185375-(4-Bromophenyl)-3-methylisoxazol-4-amine

Product 1

HCID 66577607(1-Benzyl-piperidin-4-yl)-[5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-ylamine (0.500 g, 1.73 mmol) and 1-benzyl-piperidin-4-one were mixed with acetic acid (0.200 mL) in MeOH (8 mL). The reaction was cooled to 0° C. and stirred for one hour before sodium cyanoborohydride (0.108 g, 1.74 mmol) was added. The reaction was allowed to warm to room temperature and was monitored by analytical LCMS. When complete, the reaction was quenched with aqueous sodium bicarbonate then submitted to standard workup procedures. The crude material was purified by silica gel chromatography (0-100% EtOAc in hexanes) to afford the title compound

Workup

  1. additionwas added
  2. temperatureto warm to room temperature
  3. customWhen complete, the reaction was quenched with aqueous sodium bicarbonate
  4. customThe crude material was purified by silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ff112993a7724bc692c3532bd186a8e0
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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