2-(Methylamino)ethanol → HCID 11355749, compound

HRID 2229217Notes

Reaction equation

HRID 2229217 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].[S:6]1[CH:10]=[CH:9][C:8]([CH:11]=O)=[CH:7]1.[BH3-]C#N.[Na+]>CO.CC(O)=O>[CH3:1][N:2]([CH2:11][C:8]1[CH:9]=[CH:10][S:6][CH:7]=1)[CH2:3][CH2:4][OH:5]

Participants

6

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 681353-ThiophenecarboxaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 11355749HCID 11355749, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

2-(Methylamino)-ethanol (0.047 mol, 3.5 g) and 3-thiophenecarboxaldehyde (0.047 mol, 5.3 g) were dissolved in 50 mL of MeOH and 10 mL of AcOH. NaCNBH3 (0.023 mol, 1.5 g) was added portionwise, and the resulting mixture was stirred for 18 h. The solvent was removed in vacuo, and the residue was taken up in 1N KOH and extracted with EtOAc. The organics were dried and concentrated to give an oil which was filtered through a six inch silica gel plug using 1:1 hexanes:ethyl acetate to give 7.6 g of product. 1H NMR (300 MHz) CDCl3: 7.3 (m, 1H), 7.12 (s, 1H), 7.05 (d, 1H), 3.6 (m, 4H), 2.57 (t, 2H), 2.25 (s, 3H).

Workup

  1. customThe solvent was removed in vacuo
  2. extractionextracted with EtOAc
  3. customThe organics were dried
  4. concentrationconcentrated
  5. customto give an oil which
  6. filtrationwas filtered through a six inch silica gel plug

Sources & evidence

ORD record
ord-ae4c30c00f0043078b37b617f52d40bc
Source dataset
uspto-grants-2002_07
Patent number
US06420383B1

Reaction notes

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