Water → 3,4,5,6,7,8-Hexahydrobenzo[4,5]thieno[2,3-c]pyridin-1(2H)-one

HRID 1024019Notes

Reaction equation

HRID 1024019 reaction equation
[CH2:1]1[C:5]2[C:6]3[CH2:12][CH2:11][CH2:10][CH2:9][C:7]=3[S:8][C:4]=2[C:3](=[N:13]O)[CH2:2]1.[OH2:15]>>[C:3]1(=[O:15])[C:4]2[S:8][C:7]3[CH2:9][CH2:10][CH2:11][CH2:12][C:6]=3[C:5]=2[CH2:1][CH2:2][NH:13]1

Participants

3

Reactant 2

HCID 962WaterHCID 766717265,6,7,8-Tetrahydro-1H-benzo[b]cyclopenta[d]thiophen-3(2H)-one Oxime

Product 1

HCID 208997543,4,5,6,7,8-Hexahydrobenzo[4,5]thieno[2,3-c]pyridin-1(2H)-oneYield 75%

Conditions

Temperature
80 °C

Procedure

A 50-mL single-neck round-bottomed flask equipped with a reflux condenser, magnetic stirrer and nitrogen inlet was charged with 103d (285 mg, 1.38 mmol) and polyphosphoric acid (15 g). After stirring at 80° C. for 16 h, the reaction mixture was cooled to room temperature, and water (30 mL) was added. The resulting mixture was stirred for 30 min and filtered. The filter cake was washed with water (20 mL) and dried in a vacuum oven at 45° C. to afford a 75% yield (215 mg) of 103e as an off-white solid: mp 203° C. dec; 1H NMR (500 MHz, CDCl3) δ 5.62 (s, 1H), 3.59 (t, 2H, J=7.0 Hz), 2.81 (t, 2H, J=6.0 Hz), 2.72 (t, 2H, J=7.0 Hz), 2.48 (t, 2H, J=6.0 Hz), 1.84 (m, 4H). MS (APCI+) m/z 208.3 (M+H)

Workup

  1. customA 50-mL single-neck round-bottomed flask equipped with a reflux condenser, magnetic stirrer and nitrogen inlet
  2. temperaturethe reaction mixture was cooled to room temperature
  3. stirringThe resulting mixture was stirred for 30 min
  4. filtrationfiltered
  5. washThe filter cake was washed with water (20 mL)
  6. customdried in a vacuum oven at 45° C.

Sources & evidence

ORD record
ord-fb5377dba9e842ef935fb3de5b24a9de
Source dataset
uspto-grants-2014_05
Patent number
US08722676B2

Reaction notes

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