Methyl iodide → 2,3,4,5-tetrahydro-alpha-methyl-1-methyl-1H-1-benzazepine-7-methanol

HRID 37420Notes

Reaction equation

HRID 37420 reaction equation
[Mg].[CH3:2]I.[CH3:4][N:5]1[C:11]2[CH:12]=[CH:13][C:14]([CH:16]=[O:17])=[CH:15][C:10]=2[CH2:9][CH2:8][CH2:7][CH2:6]1.[Cl-].[NH4+]>CCOCC>[CH3:2][CH:16]([C:14]1[CH:13]=[CH:12][C:11]2[N:5]([CH3:4])[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:15]=1)[OH:17]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 19935434HCID 19935434, compound

Product 1

HCID 199353992,3,4,5-tetrahydro-alpha-methyl-1-methyl-1H-1-benzazepine-7-methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The Grignard reagent was prepared from 1.04 g of magnesium shavings and 2.30 ml of methyl iodide under argon in 40 ml of absolute ether. To this Grignard solution was slowly added dropwise at room temperature a solution of 4.38 g of 2,3,4,5-tetrahydro-1-methyl-1H-1-benzazepine-7-carboxaldehyde in 10 ml of ether. The reaction mixture was stirred for 2 hours. Thereafter, the mixture was hydrolyzed with saturated ammonium chloride solution, extracted with ether, washed with water and dried. After evaporation, there were obtained 4.47 g of 2,3,4,5-tetrahydro-α-methyl-1-methyl-1H-1-benzazepine-7-methanol as a yellow oil.

Workup

  1. extractionextracted with ether
  2. washwashed with water
  3. customdried
  4. customAfter evaporation

Sources & evidence

ORD record
ord-fc8e9b8ab68e43a1a3073916e1d637d1
Source dataset
uspto-grants-1995_05
Patent number
US05420273

Reaction notes

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