Sodium borohydride → HCID 68466810, compound

HRID 502997Notes

Reaction equation

HRID 502997 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2([C:12]3[N:16]4[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:15]4=[N:14][N:13]=3)[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:3][CH2:2]1.N1(CO)C=[CH:26]N=N1.[BH4-].[Na+]>CO>[CH3:26][N:1]1[CH2:6][CH2:5][CH:4]([C:7]2([C:12]3[N:16]4[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:15]4=[N:14][N:13]=3)[CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 15568557HCID 15568557, compound3×HCID 68465905HCID 68465905, compound

Product 1

HCID 68466810HCID 68466810, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

3-(1-Piperidin-4-ylcyclopentyl)-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine (263 mg) and 1H-triazole-1-methanol (86 mg) were diluted with methanol (4 ml), followed by stirring at 60° C. for 1 hour. After 1H-triazole-1-methanol (93 mg) was added thereto and the whole was stirred for 1 hour, 1H-triazole-1-methanol (107 mg) was further added and the whole was stirred for 1 hour. The reaction solution was cooled to room temperature and then sodium borohydride (91 mg) was added thereto, followed by stirring at room temperature for 16 hours. The reaction solution was subjected to evaporation under reduced pressure and the resulting residue was diluted with a 1M aqueous sodium hydroxide solution (30 ml), followed by extraction with chloroform (15 ml×2). The organic layer was dried over anhydrous sodium sulfate and filtered and then the solvent was removed by evaporation under reduced pressure. The resulting residue was purified by column chromatography (methanol:chloroform=1:6) and then the resulting solid washed with hexane to obtain 105 mg of 3-[1-(1-methyl-4-piperidinyl)cyclopentyl]-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine (white solid).

Workup

  1. stirringthe whole was stirred for 1 hour
  2. stirringthe whole was stirred for 1 hour
  3. temperatureThe reaction solution was cooled to room temperature
  4. stirringby stirring at room temperature for 16 hours
  5. customThe reaction solution was subjected to evaporation under reduced pressure
  6. additionthe resulting residue was diluted with a 1M aqueous sodium hydroxide solution (30 ml)
  7. extractionfollowed by extraction with chloroform (15 ml×2)
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customthe solvent was removed by evaporation under reduced pressure
  11. customThe resulting residue was purified by column chromatography (methanol:chloroform=1:6)
  12. washthe resulting solid washed with hexane

Sources & evidence

ORD record
ord-96fb1b89cc574a68be855b17d933fdb8
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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