Ethyl bromoacetate → [4-(2,3-Dihydro-benzofuran-5-carbonyl)-piperidin-1-yl]-acetic acid ethyl ester

HRID 713452Notes

Reaction equation

HRID 713452 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)=[O:11])=[CH:9][C:4]=2[CH2:3][CH2:2]1.Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(N(CC)CC)C>C(#N)C>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][N:15]1[CH2:14][CH2:13][CH:12]([C:10]([C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][CH2:3][C:4]=3[CH:9]=2)=[O:11])[CH2:17][CH2:16]1)[CH3:24]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 24688984(2,3-dihydro-5-benzofuranyl)-4-piperidinylMethanone

Product 1

HCID 71227106[4-(2,3-Dihydro-benzofuran-5-carbonyl)-piperidin-1-yl]-acetic acid ethyl esterYield 41.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of (2,3-dihydro-benzofuran-5-yl)-piperidin-4-yl-methanone (0.30 g, 1.30 mmol) in acetonitrile (10 mL) was added ethyl 2-bromoacetate (0.26 g, 1.6 mmol) and triethylamine (0.66 g, 6.5 mmol). The mixture was heated at 85° C. overnight, the solvent was evaporated under reduced pressure and purified via flash column chromatography (ethyl acetate:heptane) to provide desired product as a white solid (0.18 g, 0.54 mmol). MS (ESI) m/z 317.8 (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 1.22 min.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. custompurified via flash column chromatography (ethyl acetate:heptane)

Sources & evidence

ORD record
ord-f56a6df2d28a4c8298d78541b5974d9a
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

Loading…