HCID 18617418, compound → HCID 12052630, compound

HRID 1264082Notes

Reaction equation

HRID 1264082 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[C:6]([NH2:8])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:6][NH2:8]

Participants

4

Reactant 2

HCID 18617418HCID 18617418, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12052630HCID 12052630, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Methoxy-4-[(1-pyrrolidinyl)methyl]benzamide (11.2 g, 47.8 mmol) was combined with lithium aluminum hydride (3.8 g 100 mmol, 2.10 eq.) in dry THF (320 mL). The reaction was heated at reflux until all of the starting amide had been consumed by tlc (9:1 CHCl3:MeOH, 1% TEA). The reaction mixture was allowed to cool to room temperature then water (5 mL) slowly was added. After 15 min, aqueous sodium hydroxide (5 mL of 15% w/v) was added followed by more water (15 mL). After 10 min, the reaction mixture was filtered through a pad of diatomaceous earth. The solvent was removed under reduced pressure to give the amine as an amber oil (7.95 g, 76%).

Workup

  1. temperatureThe reaction was heated
  2. customhad been consumed by tlc (9:1 CHCl3:MeOH, 1% TEA)
  3. additionwater (5 mL) slowly was added
  4. additionaqueous sodium hydroxide (5 mL of 15% w/v) was added
  5. waitAfter 10 min
  6. filtrationthe reaction mixture was filtered through a pad of diatomaceous earth
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7bf5bfcaaf5340959af7a131cc05ea69
Source dataset
uspto-grants-2003_04
Patent number
US06541499B1

Reaction notes

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