Methyl chloroformate → Methyl 1,2,4,5-tetrahydro-3h-3-benzazepine-3-carboxylate

HRID 327399Notes

Reaction equation

HRID 327399 reaction equation
[OH-].[Na+].[CH2:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][NH:5][CH2:4]1.Cl[C:15]([O:17][CH3:18])=[O:16]>O>[CH3:18][O:17][C:15]([N:5]1[CH2:4][CH2:3][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6]1)=[O:16]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 14002432,3,4,5-Tetrahydro-1H-benzo(d)azepine

Product 1

HCID 22219599Methyl 1,2,4,5-tetrahydro-3h-3-benzazepine-3-carboxylateYield 958.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 150 ml of water was dissolved 4.13 g (0.10 mol). of sodium hydroxide. To the solution was added 15.27 g (10.4 mmol.) of 2,3,4,5-tetrahydro-1H-3-benzazepine. The reaction mixture was cooled with ice, and there was added dropwise 7.9 ml (0.10 mol.) of methyl chloroformate. The mixture was stirred for 2.5 hours at room temperature, then extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate and the solvent was distilled off to leave 20.46 g (96%) of 3-methoxycarbonyl-2,3,4,5-tetrahydro-1H-3-benzazepine as colorless crystals. Recrystallization from diethyl ether--n-hexane gave colorless needles, m.p. 53°-54° C. Elemental Analysis for C12H15NO2 :

Workup

  1. temperatureThe reaction mixture was cooled with ice, and there
  2. extractionextracted with dichloromethane
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-8bfa6c66847e4a33a09e03227af4c389
Source dataset
uspto-grants-1993_12
Patent number
US05273974

Reaction notes

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