HCID 3682565, compound → 3,5-di-tert-butylbenzylamine

HRID 1991537Notes

Reaction equation

HRID 1991537 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)[C:8]#[N:9])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:13]([C:11]1[CH:10]=[C:7]([CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:12]=1)[CH2:8][NH2:9])([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 3682565HCID 3682565, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 108486343,5-di-tert-butylbenzylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 3,5-di-tert-butylbenzonitrile (863 mg, 4.02 mmol) in dry THF (10 mL) at 0° C. was added lithium aluminum hydride (304 mg, 8.0 mmol) in one portion. The reaction mixture was allowed to warm to rt for 2 h, whereupon the reaction was quenched (0.2 mL water, followed by 0.2 mL 15% potassium hydroxide solution and 0.6 mL water). The reaction mixture was stirred at rt for 1 h, then filtered through diatomaceous earth (CH2Cl2 elution). The filtrate was then concentrated and used in the next reaction without further purification: 1H NMR (300 MHz, CDCl3) δ 7.33 (s, 1H), 7.16 (d, J=1.8 Hz, 2H), 3.86 (s, 2H), 1.33 (s, 18H); mass spec (CI): 203.2 (M−NH2).

Workup

  1. customwas quenched (0.2 mL water, followed by 0.2 mL 15% potassium hydroxide solution and 0.6 mL water)
  2. filtrationfiltered through diatomaceous earth (CH2Cl2 elution)
  3. concentrationThe filtrate was then concentrated
  4. customused in the next reaction without further purification

Sources & evidence

ORD record
ord-5a6fbc52a0c54bc691599fdc613044e2
Source dataset
uspto-grants-2010_01
Patent number
US07645780B2

Reaction notes

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