Hydrochloric Acid → 6-methyl-3-piperidin-4-yl-thieno[2,3-d]isoxazole Hydrochloride

HRID 2111712Notes

Reaction equation

HRID 2111712 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:18]3[S:19][CH:20]=[C:21]([CH3:22])[C:17]=3[O:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:23]>CO>[ClH:23].[CH3:22][C:21]1[C:17]2[O:16][N:15]=[C:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[C:18]=2[S:19][CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 588177444-(6-Methyl-thieno[2,3-d]isoxazol-3-yl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 231124496-methyl-3-piperidin-4-yl-thieno[2,3-d]isoxazole Hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Stir a solution of 4-(6-methyl-thieno[2,3-d]isoxazol-3-yl)-piperidine-1-carboxylic acid tert-butyl ester (8.84 mmol, 2.85 g, 1.00 equivalents) in hydrochloric acid (48.75 mL, 1 M solution in diethyl ether) and methanol (2.00 mL) at room temperature for 3.5 hours. Filter the suspension, collect the white solid and dry to yield the desired product (659 mg). Allow the mother liquor to age overnight, filter, collect the white solid and dry to yield additional desired product (1.252 g). LC/MS (ESI), m/e 223 (MH+), retention time 1.14 minutes. Condition II.

Workup

  1. filtrationFilter the suspension
  2. customcollect the white solid
  3. customdry

Sources & evidence

ORD record
ord-40a42a96f39545ab817f5cc5938fbb08
Source dataset
uspto-grants-2009_04
Patent number
US07521445B2

Reaction notes

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