Hydrochloric Acid → 4-[4-(4,5-Dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]piperidine

HRID 1802318Notes

Reaction equation

HRID 1802318 reaction equation
[C:1]1([CH:7]2[O:11][N:10]=[C:9]([C:12]3[N:13]=[C:14]([CH:17]4[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]4)[S:15][CH:16]=3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C(OCC)C.CO>ClCCl>[C:1]1([CH:7]2[O:11][N:10]=[C:9]([C:12]3[N:13]=[C:14]([CH:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)[S:15][CH:16]=3)[CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3283Diethyl EtherHCID 666187381,1-Dimethylethyl 4-[4-(4,5-dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl)-1-piperidinecarboxylate2×

Product 1

HCID 666184764-[4-(4,5-Dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl 4-[4-(4,5-dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl)-1-piperidinecarboxylate (i.e. the product of Step A) (0.815 g, 1.97 mmol) in dichloromethane (50 mL) was added a solution of hydrogen chloride and diethyl ether (2 M, 10 mL, 20 mmol). The reaction mixture was stirred at room temperature for 1 h to give a gummy precipitate. Methanol was added to dissolve the precipitate, and the reaction mixture was stirred for an additional 1 h. The reaction mixture was concentrated under reduced pressure and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate, the organic layer was dried (MgSO4) and concentrated to give the title compound as a clear oil (0.31 g), which solidified on standing.

Workup

  1. customto give a gummy precipitate
  2. dissolutionto dissolve the precipitate
  3. stirringthe reaction mixture was stirred for an additional 1 h
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  6. dry with materialthe organic layer was dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-953702ef6c5e432ebdf1bafc9696bd34
Source dataset
uspto-grants-2013_01
Patent number
US08349870B2

Reaction notes

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