1-Benzothiophene-3-carbaldehyde → HCID 11999023, compound

HRID 2061916Notes

Reaction equation

HRID 2061916 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][N:10]([S:13]([NH2:16])(=[O:15])=[O:14])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:17]1[CH:21]=[C:20]([CH:22]=O)[C:19]2[CH:24]=[CH:25][CH:26]=[CH:27][C:18]1=2.[BH4-].[Na+]>C(O)C>[S:17]1[CH:21]=[C:20]([CH2:22][NH:16][S:13]([N:10]2[CH2:9][CH2:8][CH:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:12][CH2:11]2)(=[O:15])=[O:14])[C:19]2[CH:24]=[CH:25][CH:26]=[CH:27][C:18]1=2

Participants

5

Reactant 3

HCID 2273281-Benzothiophene-3-carbaldehydeHCID 4311764Sodium borohydrideHCID 119990221-Piperidinesulfonamide, 4-phenyl-

Product 1

HCID 11999023HCID 11999023, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

4-Phenyl-piperidine-1-sulfonic acid amide (1.5 g, 6.24 mmol) was dissolved in ethanol (20 mL). Benzo[b]thiophene-3-carbaldehyde (1.0 g, 6.24 mmol) was then added and the reaction mixture was warmed to 45° C. overnight. The reaction mixture was cooled to room temperature and then treated with sodium borohydride (0.2 g, 5.29 mmol). The reaction was then quenched by addition of 1N HCl. The reaction mixture was stirred overnight. The product precipitated from solution and was removed by vacuum filtration to yield the title compound as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe reaction was then quenched by addition of 1N HCl
  3. customThe product precipitated from solution
  4. customwas removed by vacuum filtration

Sources & evidence

ORD record
ord-6e44a8b456864583bab24441660ce391
Source dataset
uspto-grants-2012_10
Patent number
US08283478B2

Reaction notes

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