Ammonia → 4-Butoxymethyl-benzylamine

HRID 1891590Notes

Reaction equation

HRID 1891590 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[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>O1CCCC1>[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%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of lithium aluminum hydride (600 mg, 13 mmol, purity: 80%) and tetrahydrofuran (10 mL) was added a mixture of 4-butoxymethyl-benzonitrile (600 mg, 3.2 mmol) described in Manufacturing Example 33-1-1 and tetrahydrofuran (10 mL) at 0° C., which was stirred for 4 hours at room temperature. 28% Aqueous ammonia solution was added dropwise to the reaction mixture at 0° C. The reaction mixture was warmed to room temperature and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (620 mg, 101%) as a crude product.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was warmed to room temperature
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-a4eb160d7dd74d2e8f2b3428978cbcb6
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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