Acetic Acid → HCID 68703833, compound

HRID 2234176Notes

Reaction equation

HRID 2234176 reaction equation
[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[CH2:5][CH2:6][NH2:7])[CH3:2].[C:11]1([CH2:17][CH:18]=O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C>[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[CH2:5][CH2:6][NH:7][CH2:18][CH2:17][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 998PhenylacetaldehydeHCID 5210291-Amino-3,3-diethoxypropaneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 68703833HCID 68703833, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,3-Diethoxypropan-1-amine (0.20 g) dissolved in ethanol (10 mL) was treated with 2-phenylacetaldehyde (0.163 g) and acetic acid (0.02 mL). The resulting mixture was stirred at room temperature for 15 minutes and treated with sodium cyanoborohydride (0.051 g). After 14 hours the mixture was concentrated, taken up in ethyl acetate (30 mL) washed with saturated sodium bicarbonate (20 mL), brine (20 mL), dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure to give a crude sample of the sub-titled compound (0.33 g).

Workup

  1. concentrationAfter 14 hours the mixture was concentrated
  2. washwashed with saturated sodium bicarbonate (20 mL), brine (20 mL)
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0422faccfcb94ff0bdf746579bb0a0ce
Source dataset
uspto-grants-2010_05
Patent number
US07709511B2

Reaction notes

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