Tetrahydrofuran → 34104-74-0

HRID 1578391Notes

Reaction equation

HRID 1578391 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[F:12][C:13]1[CH:40]=[CH:39][C:16]([C:17]([CH2:19][CH2:20][C:21]([N:23]2[CH2:28][CH2:27][CH:26]([N:29]3[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[NH:31][C:30]3=[O:38])[CH2:25][CH2:24]2)=O)=[O:18])=[CH:15][CH:14]=1>O>[F:12][C:13]1[CH:40]=[CH:39][C:16]([CH:17]([OH:18])[CH2:19][CH2:20][CH2:21][N:23]2[CH2:28][CH2:27][CH:26]([N:29]3[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[NH:31][C:30]3=[O:38])[CH2:25][CH2:24]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 21559997HCID 21559997, compound

Product 1

HCID 19370634104-74-0

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 2.0 g of lithium aluminum hydride and 180 ml of tetrahydrofuran at room temperature, was added 4.6 g of 1-[1-(β-p-fluorobenzoylpropionyl)-4-piperidyl]-2-oxobenzimidazoline portionwise over a period of about 10 minutes. The mixture was further stirred at room temperature for one hour, then gradually heated to 60°C over a period of one hour, stirred for additional 4 hours at 60° - 65°C, and then cooled in ice. To the reaction mixture was carefully added 20 milliliters of cold water, and the precipitate formed was filtered off. The filtrate was added with 6 ml of acetic acid, and the tetrahydrofuran was removed by distillation under reduced pressure. The residue was made slightly alkaline by adding a 14% aqueous ammonia, and the solid precipitated was collected by filtration, dried, and recrystallized from toluene to obtain a white crystalline powder of 1-(p-fluorophenyl)-4-[4-(2-oxo-1-benzimidazolinyl)-piperidino]-1-butanol, melting at 160° - 161° C.

Workup

  1. temperaturegradually heated to 60°C over a period of one hour
  2. stirringstirred for additional 4 hours at 60° - 65°C
  3. temperaturecooled in ice
  4. customthe precipitate formed
  5. filtrationwas filtered off
  6. additionThe filtrate was added with 6 ml of acetic acid
  7. customthe tetrahydrofuran was removed by distillation under reduced pressure
  8. additionby adding a 14% aqueous ammonia
  9. customthe solid precipitated
  10. filtrationwas collected by filtration
  11. customdried
  12. customrecrystallized from toluene

Sources & evidence

ORD record
ord-43a160b2a7b54e77806b4b82139d292c
Source dataset
uspto-grants-1976_02
Patent number
US03936468

Reaction notes

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