Water → 2,3-dihydro-6-methoxy-2-methyl-N-propyl-4-benzofuranamine

HRID 614005Notes

Reaction equation

HRID 614005 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([NH:13][C:14](=O)[CH2:15][CH3:16])[C:6]2[CH2:7][CH:8]([CH3:10])[O:9][C:5]=2[CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1C=CC=CC=1.C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[O:9][CH:8]([CH3:10])[CH2:7][C:6]2=[C:11]([NH:13][CH2:14][CH2:15][CH3:16])[CH:12]=1

Participants

6

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 21329827N-(2,3-dihydro-6-methoxy-2-methyl-4-benzofuranyl)propanamide

Product 1

HCID 213298252,3-dihydro-6-methoxy-2-methyl-N-propyl-4-benzofuranamine

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 3.2 grams of N-(2,3-dihydro-6-methoxy-2-methyl-4-benzofuranyl)propanamide, prepared in the foregoing example, in 30 cc of anhydrous benzene is gradually added into a suspension of 1.1 grams of LiAlH4 in 30 cc of anhydrous ethyl ether at 0° C. and the resulting reaction mixture is heated to the reflux temperature for 6 hours. At the end of this time the temperature is decreased to 0° C. and the aluminum complex is decomposed by addition of 3.3 cc of water. After 30 minutes of stirring at room temperature, the inorganic salts are discarded by filtration and the filtrate, dried over Na2SO4, is concentrated to dryness. The under vacuum distillation of the obtained residue affords 2.8 grams (93 percent of theoretical) of the title compound. B.p./0.2 mmHg 140°-142° C. The corresponding hydrochloride prepared by treatment of the free base with HCl melts at 110°-111° C.

Workup

  1. customthe resulting reaction mixture
  2. temperatureis heated to the reflux temperature for 6 hours
  3. customis decreased to 0° C.
  4. filtrationthe inorganic salts are discarded by filtration
  5. dry with materialthe filtrate, dried over Na2SO4
  6. concentrationis concentrated to dryness
  7. distillationThe under vacuum distillation of the obtained residue

Sources & evidence

ORD record
ord-1f2b4daed063461b9607fc13c717e348
Source dataset
uspto-grants-1979_03
Patent number
US04143055

Reaction notes

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