Sodium Hydroxide → 5-{4-[(Tert-butoxy)carbonyl]piperazin-1-yl}thiophene-2-carboxylic acid

HRID 16744

Reaction equation

HRID 16744 reaction equation
[CH:1]([C:3]1[S:7][C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1)=[O:2].[OH-:21].[Na+]>C(O)C.O.[N+]([O-])([O-])=O.[Ag+]>[CH3:18][C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][N:8]([C:6]2[S:7][C:3]([C:1]([OH:21])=[O:2])=[CH:4][CH:5]=2)[CH2:9][CH2:10]1)=[O:15])([CH3:20])[CH3:19]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 28065298Tert-butyl 4-(5-formylthiophen-2-yl)piperazine-1-carboxylate

Product 1

HCID 543134535-{4-[(Tert-butoxy)carbonyl]piperazin-1-yl}thiophene-2-carboxylic acidYield 71%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A solution of tert-butyl 4-(5-formylthien-2-yl)piperazine-1-carboxylate (2.5 1 g, 8.50 mmol) in ethanol (85 ml) was added in one portion to a solution of silver (I) nitrate (10.0 g, 58.8 mmol) and sodium hydroxide (4.83 g, 120.6 mmol) in water (85 ml). This mixture was stirred and heated at 65° C. for 22 h. The mixture was cooled by the addition of ice and then filtered to remove silver salts. The filtrate was carefully evaporated to remove the ethanol and the resulting aqueous solution was filtered again through a glass-fibre pad to remove tarry material. The filtrate was then diluted with water to a total volume of 400 ml and then acidified to pH 5 with acetic acid. The precipitate was filtered off, washed with water and then dried in a vacuum oven at 45° C. overnight to give 5-[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]thiophene-2-carboxylic acid (1.88 g, 71%).

Workup

  1. temperatureThe mixture was cooled by the addition of ice
  2. filtrationfiltered
  3. customto remove silver salts
  4. customThe filtrate was carefully evaporated
  5. customto remove the ethanol
  6. filtrationthe resulting aqueous solution was filtered again through a glass-fibre pad
  7. customto remove tarry material
  8. additionThe filtrate was then diluted with water to a total volume of 400 ml
  9. filtrationThe precipitate was filtered off
  10. washwashed with water
  11. customdried in a vacuum oven at 45° C. overnight

Sources & evidence

ORD record
ord-781faa25e190466ba8495e807b8bb176
Source dataset
uspto-grants-2010_06
Patent number
US07737149B2

Linked notes

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