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

HRID 1021598

Reaction equation

HRID 1021598 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 105d (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 105e 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-83e792165f9d4a1898774c12d6f6f9cc
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Linked notes

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