Ammonia → 3-(Piperidin-4-ylmethoxy)-4-(2,2,2-trifluoroethoxy)-1,2-benzisoxazole

HRID 2410324Notes

Reaction equation

HRID 2410324 reaction equation
[F:1][C:2]([F:30])([F:29])[CH2:3][O:4][C:5]1[C:10]2[C:11]([O:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)=[N:12][O:13][C:9]=2[CH:8]=[CH:7][CH:6]=1.O.ClCCl.N>Cl.CO>[NH:19]1[CH2:20][CH2:21][CH:16]([CH2:15][O:14][C:11]2[C:10]3[C:5]([O:4][CH2:3][C:2]([F:1])([F:29])[F:30])=[CH:6][CH:7]=[CH:8][C:9]=3[O:13][N:12]=2)[CH2:17][CH2:18]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 6344DichloromethaneHCID 69318699tert-Butyl 4-({[4-(2,2,2-trifluoroethoxy)-1,2-benzisoxazol-3-yl]oxy}methyl)piperidine-1-carboxylate

Product 1

HCID 693177283-(Piperidin-4-ylmethoxy)-4-(2,2,2-trifluoroethoxy)-1,2-benzisoxazole

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 887MethanolSolvent

Procedure

To a stirred mixture of tert-butyl 4-({[4-(2,2,2-trifluoroethoxy)-1,2-benzisoxazol-3-yl]oxy}methyl)-piperidine-1-carboxylate (3.0 g, 6.96 mmol, EXAMPLE 2, Step 1) in 10% hydrogen chloride in methanol (100 mL) was added hydrochloric acid (3.0 mL) at ambient temperature. After being stirred at room temperature for 2 h, the mixture was concentrated in vacuo to give a solid. The residual solid was dissolved with water and dichloromethane. Sat. aq. ammonia was added to the mixture and extracted with dichloromethane (100 mL×3). The extracts were combined and dried over sodium sulfate and concentrated in vacuo to give 2.31 g (quant.) of the title compound as a white solid.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customto give a solid
  3. extractionextracted with dichloromethane (100 mL×3)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-13404d2a1d784bb3ac14e30abcb4e520
Source dataset
uspto-grants-2014_08
Patent number
US08816090B2

Reaction notes

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