Tetrahydrofuran → HCID 54415633, compound

HRID 1414201Notes

Reaction equation

HRID 1414201 reaction equation
O1CCCC1.[C:6]12([C:16]([N:18]3[CH2:23][CH2:22][N:21]([C:24](=O)[CH:25]=[CH:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:20][CH2:19]3)=O)[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH2:9]3)[CH2:7]1)[CH2:13]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O>[C:6]12([CH2:16][N:18]3[CH2:19][CH2:20][N:21]([CH2:24][CH:25]=[CH:26][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:22][CH2:23]3)[CH2:13][CH:12]3[CH2:14][CH:8]([CH2:9][CH:10]([CH2:11]3)[CH2:15]1)[CH2:7]2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 68120264HCID 68120264, compound

Product 1

HCID 54415633HCID 54415633, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To 20 ml of tetrahydrofuran, 1 g of N-(1-adamantane carbonyl)-N' -cinnamoyl piperazine which was obtained in Example 1 (II) was dissolved and to this 0.24 g of lithium aluminum hydride powder were added gradually at 0° C. After refluxing for 4 hrs., it was cooled to 0° C and water was added to this at 0° C carefully to separate an organic solvent layer, subsequently the solvent was distilled away. The residues were dissolved in chloroform which was washed with water, dehydrated and then was distilled away. The residues were subjected to silica gel column chromatography (eluant: mixture of chloroform and methanol) and N-(1-adamantyl methyl)-N'-cinnamyl piperazine was obtained. Melting point of the product was 85°-87° C and the yield was 20%.

Workup

  1. additionwere added gradually at 0° C
  2. temperatureAfter refluxing for 4 hrs
  3. customto separate an organic solvent layer
  4. distillationsubsequently the solvent was distilled away
  5. dissolutionThe residues were dissolved in chloroform which
  6. washwas washed with water
  7. distillationwas distilled away
  8. additionThe residues were subjected to silica gel column chromatography (eluant: mixture of chloroform and methanol)

Sources & evidence

ORD record
ord-3fbbcb2722c743229c4cc4a8e861014a
Source dataset
uspto-grants-1977_01
Patent number
US04001223

Reaction notes

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