Acetaldehyde → HCID 14777026, compound

HRID 1844255Notes

Reaction equation

HRID 1844255 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH:11](=O)[CH3:12].[BH3-]C#N.[Na+].C(NCC)C>C1(C)C=CC=CC=1.CO>[CH2:11]([NH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[CH3:12]

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 5610TyramineHCID 8021DiethylamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 14777026HCID 14777026, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a stifling solution of tyramine (1 mM, 137 mg) and MeOH (5 mL) was added acetaldehyde in excess. Then excess NaBH3CN (1 mM, 62.8 mg) was added and the mixture stirred for 2 hours at r.t. After evaporating the solvent, methylene chloride (5 mL) was added and mixture was washed with H2O (3×5 mL). The mixture was dried over MgSO4, filtered, and evaporated to give the product in 72% yield as an orange oil. TLC (toluene:diethylamine, 4:1 v/v): RF=0.5. 1H NMR, δ: 9.48 (s, 1H), 7.14 (d, 2H), 6.70 (d, 2H), 2.85 (m, 2H), 2.60 (t, 2H), 250 (q, 2H), 2.1 (s, 1H), 1.1 (t, 3H). 13C NMR, δ: 167.5, 134.3, 130.2, 115.6, 48.2, 44.4, 35.6, 15.6. Anal. calcd for C10H15NO: C, 72.69; H, 9.15; N, 8.48%. Found; C, 72.50; H, 9.20; N, 8.50%.

Workup

  1. customAfter evaporating the solvent, methylene chloride (5 mL)
  2. additionwas added
  3. washmixture was washed with H2O (3×5 mL)
  4. dry with materialThe mixture was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give the product in 72% yield as an orange oil

Sources & evidence

ORD record
ord-52dc1e86d53b438e858bbb17190ed682
Source dataset
uspto-grants-2015_02
Patent number
US08946302B2

Reaction notes

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