Sodium Hydroxide → HCID 70558733, compound

HRID 1389135Notes

Reaction equation

HRID 1389135 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]([CH2:12][CH2:13][NH2:14])=[CH:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.[OH-].[Na+].[CH:17]1([C:20](Cl)=O)[CH2:19][CH2:18]1>C(Cl)Cl>[CH:17]1([CH2:20][NH:14][CH2:13][CH2:12][C:10]2[O:9][C:8]3[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=3[CH:11]=2)[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 77637Cyclopropanecarbonyl chloride2×HCID 66592603HCID 66592603, compound

Product 1

HCID 70558733HCID 70558733, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 10.27 g of 7-methoxy-3-benzofuranethylamine, 60 ml of methylene chloride, and 60 ml of 15% aqueous sodium hydroxide solution was added, with cooling, 8 ml of cyclopropanecarbonyl chloride. The mixture was stirred at room temperature overnight; an additional 2 ml of cyclopropanecarbonyl chloride added after two hours. The solvent was removed from the dried organic layer and the residue heated under reflux with 3.5 g of lithium aluminum hydride in tetrahydrofuran for 6 hours. Water (3.5 ml), 15% aqueous sodium hydroxide solution (3.5 ml) and finally water (10.5 ml) were added with cooling, and the mixture filtered. Removal of the solvent and short-path distillation of the residue (bath to 170°, 1 micron pressure) gave 11.74 g (90% yield) of N-cyclopropylmethyl-7-methoxy-3-benzofuranethylamine; nmr spectrum (in CDCl3): τ2.6 (s, 1); 2.8-3.4 (m, 3); 6.1 (s, 3); 7.1-7.4 (m, 4 ); 7.6 (d, J=6.5 Hz, 2) and 8.1-10.2 (m, 6).

Workup

  1. additionwas added
  2. temperaturewith cooling
  3. customThe solvent was removed from the dried organic layer
  4. temperaturethe residue heated
  5. temperatureunder reflux with 3.5 g of lithium aluminum hydride in tetrahydrofuran for 6 hours
  6. additionWater (3.5 ml), 15% aqueous sodium hydroxide solution (3.5 ml) and finally water (10.5 ml) were added
  7. temperaturewith cooling
  8. filtrationthe mixture filtered
  9. customRemoval of the solvent and short-path distillation of the residue (bath to 170°, 1 micron pressure)

Sources & evidence

ORD record
ord-130e1bc72ebc457b80d3d37c2c6d36e6
Source dataset
uspto-grants-1981_01
Patent number
US04243668

Reaction notes

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