Benzylethanolamine → Ammonia

HRID 586708Notes

Reaction equation

HRID 586708 reaction equation
[NH:1]1[CH:5]=[C:4]([CH:6]=O)[N:3]=[CH:2]1.[CH2:8]([NH:15][CH2:16][CH2:17][OH:18])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[NH3:1].[CH2:8]([N:15]([CH2:6][C:4]1[N:3]=[CH:2][NH:1][CH:5]=1)[CH2:16][CH2:17][OH:18])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 4348BenzylethanolamineHCID 764281H-Imidazole-4-carbaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 2

HCID 222AmmoniaHCID 178521303HCID 178521303, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 4-imidazolecarboxaldehyde (14 g, 145.7 mmol) and N-benzylethanolamine (26.4 g, 174.8 mmol) in tetrahydrofuran (200 mL) was stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (37.06 g, 174.8 mmol) was added portionwise over 40 minutes, and the reaction stirred at room temperature for 18 hours. The reaction was quenched by the addition of water (150 mL), the mixture neutralised using saturated sodium bicarbonate solution, and then extracted with dichloromethane (3×300 mL). The combined organic extracts were dried (MgSO4) and evaporated under reduced pressure to give a yellow oil. This was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (95:5:0 to 90:10:1) to afford the title compound, 18.1 g.

Workup

  1. stirringthe reaction stirred at room temperature for 18 hours
  2. customThe reaction was quenched by the addition of water (150 mL)
  3. extractionextracted with dichloromethane (3×300 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customevaporated under reduced pressure
  6. customto give a yellow oil
  7. customThis was purified by column chromatography on silica gel using an elution gradient of dichloromethane

Sources & evidence

ORD record
ord-12fa3c1fc2704702a28b68c94d10b62d
Source dataset
uspto-grants-2005_08
Patent number
US06936619B2

Reaction notes

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