Water → (4-Tert-butyl-benzyl)-(2-pyridin-4-yl-ethyl)-amine

HRID 855235Notes

Reaction equation

HRID 855235 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][NH2:9])=[CH:3][CH:2]=1.[C:10]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)([CH3:13])([CH3:12])[CH3:11].[BH4-].[Na+].O>CO>[C:10]([C:14]1[CH:15]=[CH:16][C:17]([CH2:18][NH:9][CH2:8][CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:20][CH:21]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 703244-tert-ButylbenzaldehydeHCID 832754-PyridineethanamineHCID 4311764Sodium borohydride

Product 1

HCID 60913740(4-Tert-butyl-benzyl)-(2-pyridin-4-yl-ethyl)-amineYield 91.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.22 g (10 mmol) of 2-(4-pyridyl)-ethyl amine and 1.62 g (10 mmol) of 4-tert-butyl benzaldehyde were dissolved in 20 ml methanol and stirred at rt over night. 555 mg (15 mmol) of sodium borohydride were added in portions under cooling. After complete addition the reaction mixture was stirred for 1 h at rt. Water was added and methanol was evaporated. The reaction mixture was extracted twice with diethyl ether. The combined organic layers were washed with water, dried over sodium sulfate, filtered and the solvent was evaporated to yield 2.45 g (91%) product as a light yellow oil. 1H NMR (DMSO-d6, 300 MHz): δ 8.49 (d, 2H), 7.34 (d, 2H) 7.21 (d, 2H), 7.13 (d, 2H), 3.77 (s, 2H), 2.93 (t, 2H), 2.81 (t, 2H), 1.31 (s, 9H).

Workup

  1. temperatureunder cooling
  2. additionAfter complete addition the reaction mixture
  3. stirringwas stirred for 1 h at rt
  4. custommethanol was evaporated
  5. extractionThe reaction mixture was extracted twice with diethyl ether
  6. washThe combined organic layers were washed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e242a4347b414e95a8e96bf70343bff4
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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