Sodium Hydroxide → HCID 178420314, compound

HRID 1162317Notes

Reaction equation

HRID 1162317 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:15]1[CH:19]=[C:18]([CH:20]=O)[N:17]=[CH:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl.C(O)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:20][C:18]2[N:17]=[CH:16][NH:15][CH:19]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 764281H-Imidazole-4-carbaldehydeHCID 4158521-Benzyl-4-piperidylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 178420314HCID 178420314, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

To a solution of 1-benzyl-4-piperidinamine (3.4 g), imidazole-4-carbaldehyde (1.4 g) and acetic acid (1.7 ml) in 1,2-dichloroethane (100 ml) was added sodium triacetoxyborohydride (4.7 g), and mixed at room temperature for 15 hours. A 1 N aqueous sodium hydroxide solution was added to the reaction solution and pH of the aqueous layer was adjusted to about 12, and then extracted with chloroform (100 ml). The extract was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain the title compound as a yellow oil (3.4 g).

Workup

  1. additionmixed at room temperature for 15 hours
  2. extractionextracted with chloroform (100 ml)
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7b3968b064494cbbb143660fa174b941
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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