Ammonia → 4-Butoxymethyl-benzylamine

HRID 1927265Notes

Reaction equation

HRID 1927265 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:11][CH2:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1)[CH2:8][CH2:9][CH3:10].N>C1COCC1>[CH2:7]([O:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][NH2:18])=[CH:19][CH:20]=1)[CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 21226445Aluminium lithium hydrideHCID 432676834-Butoxymethyl-benzonitrile

Product 1

HCID 432675904-Butoxymethyl-benzylamineYield 101.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of LAH (80%, 600 mg) and THF (10 mL) were added 4-butoxymethyl-benzonitrile (600 mg) described in Manufacturing Example 43-1 and THF (10 mL) at 0° C., which was stirred for 4 hours at room temperature. A 28% aqueous ammonia solution was added by drops to the reaction mixture at 0° C., and the excess LAH was quenched. The temperature was raised to room temperature, and then filtration was performed. The solvent was evaporated from the filtrate under a reduced pressure to obtain of the titled compound (620 mg).

Workup

  1. customthe excess LAH was quenched
  2. temperatureThe temperature was raised to room temperature
  3. filtrationfiltration
  4. customThe solvent was evaporated from the filtrate under a reduced pressure

Sources & evidence

ORD record
ord-4a4e210df7544f5293c3500909a1cea9
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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