Benzaldehyde → HCID 4247613, compound

HRID 1404760Notes

Reaction equation

HRID 1404760 reaction equation
[C:1]([CH2:3][N:4]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]#[N:11])[CH:5]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)#[N:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[Al]>C1COCC1.O>[CH:24](=[N:11][CH2:10][CH2:9][N:6]1[CH2:7][CH2:8][N:4]([CH2:3][CH2:1][N:2]=[CH:5][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 5359268AluminumHCID 11514112HCID 11514112, compound2×HCID 21226445Aluminium lithium hydride2×

Product 1

HCID 4247613HCID 4247613, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

This Example demonstrates the reduction of (3-cyanomethyl-2-phenyl-imidazolidin-1-yl)-acetonitrile (5) with LiAlH4 and protection using benzaldehyde. As shown in Scheme 3, a solution of 1 equivalent of (3-cyanomethyl-2-phenyl-imidazolidin-1-yl)-acetonitrile (5) was added to a solution of 3 equivalents of LiAlH4 in THF at about −30° C. The reaction mixture was warmed to about 20° C. over 80 minutes, whereupon thin-layer chromatography showed complete conversion. The reaction mixture was treated with water (vigorous, exothermic reaction with H2-evolution) and aluminum salts were removed by filtration. Isolation of the amine intermediate 2-[3-(2-Amino-ethyl)-2-phenyl-imidazolidin-1-yl]-ethylamine (8) as a pure compound was not readily achieved. To add protecting groups and allow isolation the amine intermediate (8) was reacted in situ with 2.2 equvialents of benzaldehyde after aqueous quench. After work-up and crystallization from acetonitrile, crystalline benzylidene-(2-{3-[2-(benzylidene-amino)-ethyl]-2-phenyl-imidazolidin-1-yl}-ethyl)-amine (7) was obtained in 32% yield and with a purity of 95.8 area % by gas chromatography.

Workup

  1. customwere removed by filtration
  2. additionTo add
  3. customwas reacted in situ with 2.2 equvialents of benzaldehyde after aqueous quench
  4. customAfter work-up and crystallization from acetonitrile

Sources & evidence

ORD record
ord-17c628fa57be485996ac09b69ebe2cf3
Source dataset
uspto-grants-2014_12
Patent number
US08912362B2

Reaction notes

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