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Water → pentyl[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]amine

HRID 492294
Notes
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Reaction equation

HRID 492294 reaction equation
[C:1]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]2[N:25]([C:26]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:24]=[N:23][N:22]=2)=[CH:11][CH:10]=1)(=O)[CH2:2][CH2:3][CH2:4][CH3:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:1]([NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]2[N:25]([C:26]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:24]=[N:23][N:22]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH3:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23569449N-[[2'-(1-Trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl] Pentanamide

Product 1

HCID 19024425pentyl[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]amineYield 100%

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent

Procedure

N-Pentanoyl-N-[[2′-[N-(triphenylmethyl)tetrazol-5-yl]-1,1′-biphenyl-4-yl]methyl]amine (1.61 g) was dissolved in tetrahydrofuran (40 mL) and at room temperature, lithium aluminum hydride (340.1 mg) was added, and then the mixture was heated under reflux. Ninety minutes later, water (5 mL), a 10% aqueous solution of sodium hydroxide (5 mL) and water (5 mL) were added successively under ice bath cooling. The organic layer was separated, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. As water remained to the residue, ethyl acetate was added to conduct extraction twice from the remaining water. The organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to afford N-pentyl-N-[[2′-[N-(triphenylmethyl)tetrazol-5-yl]-1,1′-biphenyl-4-yl]methyl] amine (1.57 g). Yield: 100%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. temperaturecooling
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionwas added
  8. extractionextraction twice from the remaining water
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-558e713334c34a8ca569e6e212f7b1b1
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07531576B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes