Ammonia → 4-(5-Chloro-furan-2-ylmethyl)-benzylamine

HRID 1927251Notes

Reaction equation

HRID 1927251 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl-].[Al+3].[Cl-].[Cl-].[Cl:11][C:12]1[O:16][C:15]([CH:17](O)[C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1.N>C1COCC1>[Cl:11][C:12]1[O:16][C:15]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([CH2:22][NH2:23])=[CH:24][CH:25]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6451240Aluminum(III) Chloride2×HCID 21226445Aluminium lithium hydrideHCID 592551164-((5-Chloro-furan-2-yl)-hydroxy-methyl)-benzonitrile

Product 1

HCID 592553974-(5-Chloro-furan-2-ylmethyl)-benzylamineYield 70.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of THF (40 mL) and LAH (2.4 g) was added aluminum chloride (9.7 g) at 0° C., which was stirred until the aluminum chloride dissolved. 4-((5-Chloro-furan-2-yl)-hydroxy-methyl)-benzonitrile (2.4 g) described in Manufacturing Example 16-1 was then added thereto at 0° C., which was stirred for 4 hours and 30 minutes at room temperature. An aqueous ammonia solution was added at 0° C. to the reaction suspension, which was filtered through Celite, and the solvent was evaporated from the filtrate under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=1:2) to obtain the titled compound (1.6 g).

Workup

  1. dissolutiondissolved
  2. additionwas then added
  3. filtrationwas filtered through Celite
  4. customthe solvent was evaporated from the filtrate under a reduced pressure
  5. customThe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-a9f7d737c6df40d285c2e72ec89d0831
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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