Trifluoroacetic acid → (2,3-dihydro-5-benzofuranyl)-4-piperidinylMethanone

HRID 713451Notes

Reaction equation

HRID 713451 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:16]2[CH:17]=[CH:18][C:19]3[O:23][CH2:22][CH2:21][C:20]=3[CH:24]=2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:23]1[C:19]2[CH:18]=[CH:17][C:16]([C:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[O:15])=[CH:24][C:20]=2[CH2:21][CH2:22]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 712269604-(2,3-Dihydro-benzofuran-5-carbonyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 24688984(2,3-dihydro-5-benzofuranyl)-4-piperidinylMethanoneYield 86.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2,3-dihydro-benzofuran-5-carbonyl)-piperidine-1-carboxylic acid tert-butyl ester (0.50 g, 1.5 mmol) in 10 mL of DCM, was added 1 mL of TFA. The reaction mixture was stirred at ambient temperature for 2.5 hours then the solvent was removed by reduced pressure to yield the title product (0.3 g, 1.3 mmol). MS (ESI) m/z 232.3 (M+H+); HPLC (Novapak 150×3.9 mm C-18 column: mobile phase: 35-90% acetonitrile/water with 0.1% TFA, at 2 mL/min over 2 min.) t 1.14 min.

Workup

  1. customthe solvent was removed by reduced pressure

Sources & evidence

ORD record
ord-e3cd31fe69d246d8b3dfeec07274d8dd
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

Loading…