Water → HCID 9996198, compound

HRID 2301200Notes

Reaction equation

HRID 2301200 reaction equation
Cl[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][N:3]=1.[NH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O.CCOC(C)=O>[C:20]1([CH2:19][N:16]2[CH2:17][CH2:18][CH:13]([CH2:12][NH:11][C:2]3[C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=4[O:4][N:3]=3)[CH2:14][CH2:15]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1514444(1-Benzyl-4-piperidyl)methanamineHCID 27797803-Chloro-1,2-benzoxazole

Product 1

HCID 9996198HCID 9996198, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-chloro-1,2-benzisoxazole (0.238 g, 1.55 mmol), 4-aminomethyl-1-phenylmethyl piperidine (0.316 g, 1.55 mmol), and K2CO3 (0.214 g, 1.55 mmol) in DMSO (10 mL) was heated at 150° C. for 20 hours. The cooled reaction mixture was diluted with EtOAc (75 mL) and poured over H2O (200 mL). The organic phase was separated and washed with brine, dried (MgSO4), filtered, and concentrated. The brown oil obtained was purified by silica gel flash chromatography (4% MeOH—CH2Cl2) to give the title compound (0.084 g, 17%) as pale yellow oil.

Workup

  1. customThe cooled reaction mixture
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe brown oil obtained
  8. customwas purified by silica gel flash chromatography (4% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-555c113fead44bdabf11b8563321f5cb
Source dataset
uspto-grants-2002_12
Patent number
US06498255B2

Reaction notes

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