4-(Benzo(b)thienyl)acetic acid → HCID 18607187, compound

HRID 542218Notes

Reaction equation

HRID 542218 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([CH2:10][C:11]([OH:13])=O)=[CH:7][CH:8]=[CH:9][C:2]1=2.C(C1NC=CN=1)(C1NC=CN=1)=O.[CH3:26][NH:27][C@@H:28]1[CH2:33][CH2:32][CH2:31][CH2:30][C@H:29]1[N:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>O1CCCC1>[CH3:26][N:27]([C@@H:28]1[CH2:33][CH2:32][CH2:31][CH2:30][C@H:29]1[N:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)[C:11](=[O:13])[CH2:10][C:6]1[C:3]2[CH:4]=[CH:5][S:1][C:2]=2[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 758334-(Benzo(b)thienyl)acetic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 13822956HCID 13822956, compound

Product 1

HCID 18607187HCID 18607187, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of benzo[b]thiophene-4-acetic acid (0.50 g, 2.6 mmol) and carbonyl di-imidazole (0.46 g, 2.8 mmol) in tetrahydrofuran (5 ml) was heated with a solution of trans-(±)-N-methyl-2-(1-piperidinyl)cyclohexanamine (0.46 g, 2.3 mmol) in tetrahydrofuran (2 ml). This mixture was heated to reflux for five minutes, concentrated in vacuo, poured into saturated aqueous sodium bicarbonate (30 ml) and extracted with dichloromethane (2×20 ml) to give an oil which on trituration with diethyl ether gave trans-(±)-N-methyl-N-[2-(1-piperidinyl)cyclohexyl]benzo[b]thiophene-4-acetamide as a crystalline solid (610 mg, 72%); VmaxC=0 (liquid film) 1635 cm-1.

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux for five minutes
  3. concentrationconcentrated in vacuo
  4. additionpoured into saturated aqueous sodium bicarbonate (30 ml)
  5. extractionextracted with dichloromethane (2×20 ml)
  6. customto give an oil which on trituration with diethyl ether

Sources & evidence

ORD record
ord-92e69a35e464461a8a3aef948266d507
Source dataset
uspto-grants-1987_04
Patent number
US04656182

Reaction notes

Loading…