Formaldehyde → Ethyl 3-(dimethylamino)benzenepropanoate

HRID 1199087Notes

Reaction equation

HRID 1199087 reaction equation
Cl.N[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1.C=O.[C:18]([BH3-])#[N:19].[Na+].[C:22](O)(=O)CC>CO>[CH3:22][N:19]([CH3:18])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1032Propionic AcidHCID 5003444Sodium cyanoborohydrideHCID 13910793HCID 13910793, compound

Product 1

HCID 14879061Ethyl 3-(dimethylamino)benzenepropanoateYield 77.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 98.5 g (0.43 moles) of ethyl 3-aminobenzenepropanoate hydrochloride in 1500 ml of methanol and 400 ml 37% aqueous formaldehyde (4.3 moles) was added 74 g (1.16 moles) of sodium cyanoborohydride. The reaction was allowed to stir overnight under a nitrogen atmosphere. After 425 ml (5.16 moles) of propionic acid were added, the reaction mixture was refluxed for 4.5 hours. The methanol was evaporated in vacuo and the residue was brought to pH 6.8 by 25% sodium hydroxide addition. The mixture was extracted with diethyl ether which was washed with water, brine solution and dried over anhydrous potassium carbonate. The ether was evaporated in vacuo and the residue was distilled in a Kugelrohr under reduced pressure to give 74.04 g of ethyl 3-dimethylaminobenzenepropanoate, mp 94°-98° C. (oxalate), (72.1% yield).

Workup

  1. temperaturethe reaction mixture was refluxed for 4.5 hours
  2. customThe methanol was evaporated in vacuo
  3. additionthe residue was brought to pH 6.8 by 25% sodium hydroxide addition
  4. extractionThe mixture was extracted with diethyl ether which
  5. washwas washed with water, brine solution
  6. dry with materialdried over anhydrous potassium carbonate
  7. customThe ether was evaporated in vacuo
  8. distillationthe residue was distilled in a Kugelrohr under reduced pressure

Sources & evidence

ORD record
ord-85c1d79ddd994d0789b08480b12db76b
Source dataset
uspto-grants-1990_02
Patent number
US04898889

Reaction notes

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