Formaldehyde → 1-(2,3-Dihydro-1,4-benzodioxin-6-yl)-3-(dimethylamino)propan-1-one

HRID 469900Notes

Reaction equation

HRID 469900 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([C:11](=[O:13])[CH3:12])[CH:9]=[CH:10][C:2]1=2.Cl.[CH3:15][NH:16][CH3:17].[CH2:18]=O>Cl.C(O)C>[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([C:11](=[O:13])[CH2:12][CH2:15][N:16]([CH3:18])[CH3:17])[CH:9]=[CH:10][C:2]1=2

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 761431,4-Benzodioxan-6-yl methyl ketone

Product 1

HCID 28250181-(2,3-Dihydro-1,4-benzodioxin-6-yl)-3-(dimethylamino)propan-1-oneYield 82%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)ethanone (XV) (11 mmol), dimethylamine hydrochloride (14 mmol), paraformaldehyde (16 mmol) and 12 N HCl (2 drops) in ethanol (5 mL) was refluxed overnight. The solution was cooled to room temperature and the ethanol was evaporated under vacuum. The residue was treated with ethyl acetate, heated slightly and sonicated to disperse into fine particles. The solids were filtered and dried at room temperature to produce 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(dimethylamino)propan-1-one (XVI) as a white solid, (82% yield), 1H NMR (CDCl3, 400 MHz): δ ppm 2.77 (s, 6H), 3.41 (m, 2H), 3.56 (m, 2H), 4.25 (m, 4H), 6.85 (m, 1H), 7.45 (m, 2H).

Workup

  1. customthe ethanol was evaporated under vacuum
  2. additionThe residue was treated with ethyl acetate
  3. temperatureheated slightly
  4. customsonicated
  5. additionto disperse into fine particles
  6. filtrationThe solids were filtered
  7. customdried at room temperature

Sources & evidence

ORD record
ord-bf34c636d63443c397514f67538c9206
Source dataset
uspto-grants-2014_01
Patent number
US08629176B1

Reaction notes

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