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Benzenepropanal → 6-{[({[3-(dimethylamino)phenyl](1-methyl-1H-tetrazol-5-yl)methylene}amino)oxy]methyl}-N-(3-phenylpropyl)pyridin-2-amine

HRID 1258602
Notes
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Reaction equation

HRID 1258602 reaction equation
[CH3:1][N:2]([CH3:26])[C:3]1[CH:4]=[C:5]([C:9](=[N:16][O:17][CH2:18][C:19]2[N:24]=[C:23]([NH2:25])[CH:22]=[CH:21][CH:20]=2)[C:10]2[N:14]([CH3:15])[N:13]=[N:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1.[C:27]1([CH2:33][CH2:34][CH:35]=O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl.[OH-].[Na+]>[CH3:1][N:2]([CH3:26])[C:3]1[CH:4]=[C:5]([C:9](=[N:16][O:17][CH2:18][C:19]2[N:24]=[C:23]([NH:25][CH2:35][CH2:34][CH2:33][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:22]=[CH:21][CH:20]=2)[C:10]2[N:14]([CH3:15])[N:13]=[N:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 7707BenzenepropanalHCID 5049666Sodium triacetoxyborohydrideHCID 866531516-{[({[3-(dimethylamino)phenyl](1-methyl-1H-tetrazol-5-yl)methylene}amino)oxy]methyl}pyridin-2-amine

Product 1

HCID 866531526-{[({[3-(dimethylamino)phenyl](1-methyl-1H-tetrazol-5-yl)methylene}amino)oxy]methyl}-N-(3-phenylpropyl)pyridin-2-amineYield 47%

Reagents, catalysts & solvents 3

HCID 11
1,2-Dichloroethane
Solvent
HCID 6344DichloromethaneSolvent
HCID 14798Sodium HydroxideSolvent

Procedure

To a stirred solution of 6-{[({[3-(dimethylamino)phenyl](1-methyl-1H-tetrazol-5-yl)methylene}amino)oxy]methyl}pyridin-2-amine (125.0 mg, 0.35 mmol) in dry 1,2-dichloroethane (10 mL), under argon atmosphere, were added 3-phenylpropionaldehyde (66.6 mg, 0.49 mmol) and sodium triacetoxyborohydride (135 mg, 0.63 mmol) at room temperature. After stirring at room temperature for 18 h, the reaction mixture was diluted with dichloromethane (50 mL) and aq. NaOH (1 M, 30 mL) was added. After phase separation, the organic layer was washed with water (40 mL), dried over MgSO4 and concentrated in vacuo. Purification on silica gel afforded 6-{[({[3-(dimethylamino)phenyl](1-methyl-1H-tetrazol-5-yl)methylene}amino)oxy]methyl}-N-(3-phenylpropyl)pyridin-2-amine as an oil [82 mg, yield 47%; HPLC/MS: m/z=471 (M+H); logP(HCOOH)=2.57].

Workup

  1. additionwas added
  2. customAfter phase separation
  3. washthe organic layer was washed with water (40 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification on silica gel

Sources & evidence

ORD record
ord-be013236d6504d44aa4ab362a97325e1
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08466176B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes