Potassium Carbonate → N-(2,2-diethoxyethyl)-2,3-dihydrobenzo[b]furan-4-amine

HRID 1781321Notes

Reaction equation

HRID 1781321 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([NH2:10])[C:4]=2[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:17]([O:19][CH:20]([O:23][CH2:24][CH3:25])[CH2:21]Br)[CH3:18]>CN(C=O)C>[CH2:17]([O:19][CH:20]([O:23][CH2:24][CH3:25])[CH2:21][NH:10][C:9]1[C:4]2[CH2:3][CH2:2][O:1][C:5]=2[CH:6]=[CH:7][CH:8]=1)[CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 117010432,3-Dihydro-1-benzofuran-4-amine

Product 1

HCID 19046252N-(2,2-diethoxyethyl)-2,3-dihydrobenzo[b]furan-4-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,3-dihydro-benzofuran-4-ylamine (preparation. J. Hetereocyclic Chem., 18, 1333 (1980)) (4.34 g), potassium carbonate (8.87 g) and bromo acetaldehyde diethyl acetal (9.7 ml) in dry DMF (60 ml) was heated to 100° C. for 2 days under. The mixture was cooled and was partitioned between water and ethyl acetate. The dried extracts were evaporated and the residue chromatographed on silica gel (250 g). Elution with ethyl acetate:cyclohexane 1:4 gave the title compound as a pale yellow oil (4.95 g).

Workup

  1. temperatureThe mixture was cooled
  2. customwas partitioned between water and ethyl acetate
  3. customThe dried extracts were evaporated
  4. customthe residue chromatographed on silica gel (250 g)
  5. washElution with ethyl acetate:cyclohexane 1:4

Sources & evidence

ORD record
ord-83e005a4175642fe9afc52764d88855b
Source dataset
uspto-grants-1997_05
Patent number
US05633276

Reaction notes

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